Active Compound Combinations Having Insecticidal Properties

ABSTRACT

The invention relates to novel insecticidal active compound combinations comprising, firstly, anthranilamides and, secondly, further insecticidally active compounds as defined in the description, which combinations are highly suitable for controlling animal pests, such as insects.

The present invention relates to novel active compound combinationscomprising, firstly, known anthranilamides and, secondly, further knowninsecticidally active compounds, which combinations are highly suitablefor controlling animal pests, such as insects.

It is already known that certain anthranilamides have insecticidalproperties (WO 01/70671, WO 02/094791, WO 03/015519, WO 03/016284, WO03/015518, WO 03/024222, WO 03/016282, WO 03/016283, WO 03/062226, WO03/027099).

The generic formulae and definitions described in these publications,and the individual compounds described therein, are expresslyincorporated herein by way of reference.

Furthermore, it is already known than numerous heterocycles, organotincompounds, benzoylureas and pyrethroids have insecticidal and acaricidalproperties (cf. WO 93/22297, WO 93/10083, DE-A 26 41 343, EP-A 347 488,EP-A 210 487, U.S. Pat. No. 3,364,177 and EP-A 234 045). However, theactivity of these compounds is likewise not always satisfactory.

It has now been found that mixtures of anthranilamides of the formula(I)

in which

-   A¹ and A² independently of one another represent oxygen or sulfur,-   X¹ represents N or CR¹⁰,-   R¹ represents hydrogen or represents C₁-C₆-alkyl, C₂-C₆-alkenyl,    C₂-C₆-alkynyl or C₃-C₆-cycloalkyl, each of which is optionally mono-    or polysubstituted, where the substituents independently of one    another may be selected from the group consisting of R⁶, halogen,    cyano, nitro, hydroxyl, C₁-C₄-alkoxy, C₁-C₄-alkylsulfonyl,    C₂-C₄-alkoxycarbonyl, C₁-C₄-alkylamino, C₂-C₈-dialkylamino,    C₃-C₆-cycloalkylamino, (C₁-C₄-alkyl)-C₃-C₆-cycloalkylamino and R¹¹,-   R² represents hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₃-C₆-cycloalkyl, C₁-C₄-alkoxy, C₁-C₄-alkylamino,    C₂-C₈-dialkylamino, C₃-C₆-cycloalkylamino, C₂-C₆-alkoxycarbonyl or    C₂-C₆-alkylcarbonyl,-   R³ represents hydrogen, R¹¹ or represents C₁-C₆-alkyl,    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, each of which is    optionally mono- or polysubstituted, where the substituents    independently of one another may be selected from the group    consisting of R⁶, halogen, cyano, nitro, hydroxyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,    C₁-C₄-alkylsulfonyl, C₂-C₆-alkoxycarbonyl, C₂-C₆-alkylcarbonyl,    C₃-C₆-trialkylsilyl, R¹¹, phenyl, phenoxy and a 5- or 6-membered    heteroaromatic ring, where each phenyl, phenoxy and 5- or 6-membered    heteroaromatic ring may optionally be substituted and where the    substituents independently of one another may be selected from one    to three radicals W or one or more radicals R¹², or-   R² and R³ may be attached to one another and form the ring M,-   R⁴ represents hydrogen, C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₃-C₆-cycloalkyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,    C₂-C₆-haloalkynyl, C₃-C₆-halocycloalkyl, halogen, cyano, nitro,    hydroxyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio,    C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylamino,    C₂-C₈-dialkylamino, C₃-C₆-cycloalkylamino, C₃-C₆-trialkylsilyl or    represents phenyl, benzyl or phenoxy, each of which is optionally    mono- or polysubstituted, where the substituents independently of    one another may be selected from the group consisting of    C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,    C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₄-haloalkynyl,    C₃-C₆-halocycloalkyl, halogen, cyano, nitro, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl,    C₁-C₄-alkylamino, C₂-C₈-dialkylamino, C₃-C₆-cycloalkylamino,    C₃-C₆-(alkyl)cycloalkylamino, C₂-C₄-alkylcarbonyl,    C₂-C₆-alkoxycarbonyl, C₂-C₆-alkylaminocarbonyl,    C₃-C₈-dialkylaminocarbonyl and C₃-C₆-trialkylsilyl,-   R⁵ and R⁸ in each case independently of one another represent    hydrogen, halogen or represent in each case optionally substituted    C₁-C₄-alkyl, C₁-C₄-haloalkyl, R¹², G, J, —OJ, —OG, —S(O)_(p)-J,    —S(O)_(p)-G, —S(O)_(p)-phenyl, where the substituents independently    of one another may be selected from one to three radicals W or from    the group consisting of R¹², C₂-C₆-alkenyl, C₂-C₆-alkynyl,    C₁-C₄-alkoxy and C₁-C₄-alkylthio, where each substituent may be    substituted by one or more substituents independently of one another    selected from the group consisting of G, J, R⁶, halogen, cyano,    nitro, amino, hydroxyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,    C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio,    C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylamino,    C₂-C₈-dialkylamino, C₃-C₆-trialkylsilyl, phenyl and phenoxy, where    each phenyl or phenoxy ring may optionally be substituted and where    the substituents independently of one another may be selected from    one to three radicals W or one or more radicals R¹²,-   G in each case independently of one another represents a 5- or    6-membered non-aromatic carbocyclic or heterocyclic ring which may    optionally contain one or two ring members from the group consisting    of C(═O), SO and S(═O)₂ and which may optionally be substituted by    one to four substituents independently of one another selected from    the group consisting of C₁-C₂-alkyl, halogen, cyano, nitro and    C₁-C₂-alkoxy, or independently of one another represents    C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₇-cycloalkyl,    (cyano)-C₃-C₇-cycloalkyl, (C₁-C₄-alkyl)-C₃-C₆-cycloalkyl,    (C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, where each cycloalkyl,    (alkyl)cycloalkyl and (cycloalkyl)alkyl may optionally be    substituted by one or more halogen atoms,-   J in each case independently of one another represents an optionally    substituted 5- or 6-membered heteroaromatic ring, where the    substituents independently of one another may be selected from one    to three radicals W or one or more radicals R¹²,-   R⁶ independently of one another represents —C(=E¹)R¹⁹, -LC(=E1)R¹,    —C(=E¹)LR¹⁹, -LC(=E¹)LR¹⁹, —OP(=Q)(OR¹⁹)₂, —SO₂LR¹⁸ or -LSO₂LR¹⁹,    where each E¹ independently of one another represents O, S, N—R¹⁵,    N—OR¹⁵, N—N(R¹⁵)₂, N—S═O, N—CN or N—NO₂,-   R⁷ represents hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen,    C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio,    C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl,-   R⁹ represents C₁-C₄-haloalkyl, C₁-C₄-haloalkoxy,    C₁-C₄-haloalkylsulfinyl or halogen,-   R¹⁰ represents hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen,    cyano or C₁-C₄-haloalkoxy,-   R¹¹ in each case independently of one another represents in each    case optionally mono- to trisubstituted C₁-C₆-alkylthio,    C₁-C₆-alkylsulfenyl, C₁-C₆-haloalkylthio, C₁-C₆-haloalkylsulfenyl,    phenylthio or phenylsulfenyl, where the substituents independently    of one another may be selected from the list W, —S(O)_(n)N(R¹⁶)₂,    —C(═O)R¹³, -L(C═O)R¹⁴, —S(C═O)LR¹⁴, —C(═O)LR¹³,    —S(O)_(n)NR¹³C(═O)R¹³, —S(O)_(n)NR¹³C(═O)LR¹⁴ or    —S(O)_(n)NR¹³S(O)₂LR¹⁴,-   L in each case independently of one another represents O, NR¹⁸ or S,-   R¹² in each case independently of one another represents —B(OR¹⁷)₂,    amino, SH, thiocyanato, C₃-C₈-trialkylsilyloxy, C₁-C₄-alkyl    disulfides, —SF₅, —C(=E¹)R¹⁹, -LC(=E¹)R¹⁹, —C(=E¹)LR¹⁹,    -LC(=E¹)LR¹⁹, —OP(=Q)(OR¹⁹)₂, —SO₂LR¹⁹ or -LSO₂LR¹⁹,-   Q represents O or S,-   R¹³ in each case independently of one another represents hydrogen or    represents in each case optionally mono- or polysubstituted    C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl or C₃-C₆-cycloalkyl, where    the substituents independently of one another may be selected from    the group consisting of R⁶, halogen, cyano, nitro, hydroxyl,    C₁-C₄-alkoxy, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,    C₁-C₄-alkylamino, C₂-C₈-dialkylamino, C₃-C₆-cycloalkylamino or    (C₁-C₄-alkyl)-C₃-C₆-cycloalkylamino,-   R¹⁴ in each case independently of one another represents in each    case optionally mono- or polysubstituted C₁-C₂₀-alkyl,    C₂-C₂₀-alkenyl, C₂-C₂₀-alkynyl or C₃-C₆-cycloalkyl, where the    substituents independently of one another may be selected from the    group consisting of R⁶, halogen, cyano, nitro, hydroxyl,    C₁-C₄-alkoxy, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,    C₁-C₄-alkylamino, C₂-C₈-dialkylamino, C₃-C₆-cycloalkylamino and    (C₁-C₄-alky)-C₃-C₆-cycloalkylamino or represent optionally    substituted phenyl, where the substituents independently of one    another may be selected from one to three radicals W or one or more    radicals R¹²,-   R¹⁵ in each case independently of one another represents hydrogen or    represents in each case optionally mono- or polysubstituted    C₁-C₆-haloalkyl or C₁-C₆-alkyl, where the substituents independently    of one another may be selected from the group consisting of cyano,    nitro, hydroxyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio,    C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylamino,    C₂-C₈-dialkylamino, C₂-C₆-alkoxycarbonyl, C₂-C₆-alkylcarbonyl,    C₃-C₆-trialkylsilyl and optionally substituted phenyl, where the    substituents independently of one another may be selected from one    to three radicals W or one or more radicals R¹², or N(R¹⁵)₂    represents a cycle which forms the ring M,-   R¹⁶ represents C₁-C₁₂-alkyl or C₁-C₁₂-haloalkyl, or N(R¹⁶)₂    represents a cycle which forms the ring M,-   R¹⁷ in each case independently of one another represents hydrogen or    C₁-C₄-alkyl, or B(OR¹⁷)₂ represents a ring in which the two oxygen    atoms are attached via a chain having two to three carbon atoms    which are optionally substituted by one or two substituents    independently of one another selected from the group consisting of    methyl and C₂-C₆-alkoxycarbonyl,-   R¹⁸ in each case independently of one another represents hydrogen,    C₁-C₆-alkyl or C₁-C₆-haloalkyl, or N(R¹³)(R¹⁸) represents a cycle    which forms the ring M,-   R¹⁹ in each case independently of one another represents hydrogen or    represents in each case mono- or polysubstituted C₁-C₆-alkyl, where    the substituents independently of one another may be selected from    the group consisting of cyano, nitro, hydroxyl, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl,    C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl,    C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylamino, C₂-C₈-dialkylamino, CO₂H,    C₂-C₆-alkoxycarbonyl, C₂-C₆-alkylcarbonyl, C₃-C₆-trialkylsilyl and    optionally substituted phenyl, where the substituents independently    of one another may be selected from one to three radicals W,    C₁-C₆-haloalkyl, C₃-C₆-cycloalkyl or phenyl or pyridyl, each of    which is optionally mono- to trisubstituted by W,-   M in each case represents an optionally mono- to tetrasubstituted    ring which, in addition to the nitrogen atom attached to the    substituent pair R¹³ and R¹⁸, (R¹⁵)₂ or (R¹⁶)₂, contains two to six    carbon atoms and optionally additionally a further nitrogen, sulfur    or oxygen atom, where the substituents independently of one another    may be selected from the group consisting of C₁-C₂-alkyl, halogen,    cyano, nitro and C₁-C₂-alkoxy,-   W in each case independently of one another represents C₁-C₄-alkyl,    C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl,    C₂-C₄-haloalkenyl, C₂-C₄-haloalkynyl, C₃-C₆-halocycloalkyl, halogen,    cyano, nitro, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,    C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alkylamino,    C₂-C₈-dialkylamino, C₃-C₆-cycloalkylamino,    (C₁-C₄-alkyl)-C₃-C₆-cycloalkylamino, C₂-C₄-alkylcarbonyl,    C₂-C₆-alkoxycarbonyl, CO₂H, C₂-C₆-alkylaminocarbonyl,    C₃-C₈-dialkylaminocarbonyl or C₃-C₆-trialkylsilyl,-   n in each case independently of one another represents 0 or 1,-   p in each case independently of one another represents 0, 1 or 2,-   where, if (a) R⁵ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,    C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₄haloalkoxy,    C₁-C₄-haloalkylthio or halogen and (b) R⁸ represents hydrogen,    C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,    C₁-C₄-haloalkoxy, C₁-C₄-haloalkylthio, halogen, C₂-C₄-alkylcarbonyl,    C₂-C6-alkoxycarbonyl, C₂-C₆-alkylaminocarbonyl or C₃-C₈    dialkylaminocarbonyl, (c) at least one substituent selected from the    group consisting of R⁶, R¹¹ and R¹² if present and (d) if R¹² is not    present, at least one of the radicals R⁶ and R¹¹ is different from    C₂-C₆-alkylcarbonyl, C₂-C₆-alkoxycarbonyl, C₂-C₆-alkylaminocarbonyl    and C₃-C₈-dialkylaminocarbonyl, and-   where the compound of the general formula (I) may also be an N-oxide    or salt,-   and at least one insecticidally active compound from groups 2 below,    selected from-   A) benzoylureas, preferably    -   (2-1) chlorfluazuron (known from DE-A 28 18 830)

and/or

-   -   (2-2) diflubenzuron (known from DE-A 21 23 236)

and/or

-   -   (2-3) lufenuron (known from EP-A 0 179 022)

and/or

-   -   (2-4) teflubenzuron (known from EP-A 0 052 833)

and/or

-   -   (2-5) triflumuron (known from DE-A 26 01 780)

and/or

-   -   (2-6) novaluron (known from U.S. Pat. No. 4,980,376)

and/or

-   -   (2-7) hexaflumuron (known from EP-A 0 071 279)

and/or

-   -   (2-8) bistrifluoron (DBI-3204) (known from WO 98/00394)

and/or

-   -   (2-22) flufenoxuron (known from EP-A 0 161 019)

-   and/or-   B) macrolides, preferably    -   (2-9) emamectin (known from EP-A 0 089 202)-   and/or-   C) diacylhydrazines, preferably    -   (2-10) methoxyfenozide (known from EP-A 0 639 559)

and/or

-   -   (2-11) tebufenozide (known from EP-A-339 854)

and/or

-   -   (2-12) halofenozide (known from EP-A 0 228 564)

and/or

-   -   (2-13) chromafenozide (ANS-118) (known from EP-A 0 496 342)

and/or

-   -   (2-14) Trichogramma spp. (known from The Pesticide Manual, 11th        Edition, 1997, p. 1236)        and/or    -   (2-15) Verticillium lecanii (known from The Pesticide Manual,        11th Edition, 1997, p. 1266)        and/or    -   (2-16) fipronil (known from EP-A 0 295 117)

and/or

-   -   (2-17) ethiprole (known from DE-A 196 53 417)

and/or

-   -   (2-18) cyromazine (known from DE-A 27 36 876)

and/or

-   -   (2-19) azadirachtin (known from The Pesticide Manual, 11th        Edition, 1997, p. 59)        and/or    -   (2-20) diofenolan known from DE-A 26 55 910)

and/or

-   -   (2-21) indoxacarb (known from WO 92/11249)

are synergistically effective and suitable for controlling animal pests.

Surprisingly, the insecticidal and acaricidal activity of the activecompound combination according to the invention is considerably higherthan the sum of the activities of the individual active compounds. Anunforeseeable true synergistic effect is present, and not just anaddition of activities.

In addition to at least one active compound of the formula (I), theactive compound combinations according to the invention comprise atleast one active compound of group 2 selected from the compounds (2-1)to (2-22).

Depending inter alia on the nature of the substituents, the compounds ofthe formula (I) can be present as geometrical and/or optical isomers orisomer mixtures of varying composition which, if appropriate, can beseparated in a customary manner. The present invention provides both thepure isomers and the isomer mixtures, their preparation and-use andcompositions comprising them.

However, hereinbelow, for the sake of simplicity, only compounds of theformula (I) are referred to, although what is meant are both the purecompounds and, if appropriate, also mixtures having varying proportionsof isomeric compounds.

Preference is given to active compound combinations comprising compoundsof the formula (I-1)

in which

-   R² represents hydrogen or C₁-C₆-alkyl,-   R³ represents C₁-C₆-alkyl which is optionally substituted by one R⁶,-   R⁴ represents C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₂-haloalkoxy or    halogen,-   R⁵ represents hydrogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl,    C₁-C₂-haloalkoxy or halogen,-   R⁶ represents —C(=E²)R¹⁹, -LC(=E²)R¹⁹, —C(=E²)LR¹⁹ or -LC(=E²)LR¹⁹,    where each E² independently of one another represents O, S, N—R¹⁵,    N—OR¹⁵, N—N(R¹⁵)₂, and each L independently of one another    represents O or NR¹⁸,-   R⁷ represents C₁-C₄-haloalkyl or halogen,-   R⁹ represents C₁-C₂-haloalkyl, C₁-C₂-haloalkoxy,    S(O)_(p)—C₁-C₂-haloalkyl or halogen,-   R¹⁵ in each case independently of one another represents hydrogen or    represents in each case optionally substituted C₁-C₆-haloalkcyl or    C₁-C₆-alkyl, where the substituents independently of one another may    be selected from the group consisting of cyano, C₁-C₄-alkoxy,    C₁-C₄-haloalkoxy, C₁-C₄-alkylsulfinyl, C₁-C₄alkylsulfonyl,    C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl and    C₁-C₄-haloalkylsulfonyl,-   R¹⁸ in each case represents hydrogen or C₁-C₄-alkyl,-   R¹⁹ in each case independently of one another represents hydrogen or    C₁-C₆-alkyl,-   p independently of one another represents 0, 1, 2,-   and at least one active compound of group 2 selected from the    compounds (2-1) to (2-22).

In the radical definitions mentioned as being preferred, halogenrepresents fluorine, chlorine, bromine and iodine, in particularfluorine, chlorine and bromine

Particular preference is given to active compound combinationscomprising compounds of the formula (I-1) in which

-   R² represents hydrogen or methyl,-   R³ represents C₁-C₄-alkyl (in particular methyl, ethyl, n-,    isopropyl, n-, iso-, sec-, tert-butyl),-   R⁴ represents methyl, trifluoromethyl, trifluoromethoxy, fluorine,    chlorine, bromine or iodine,-   R⁵ represents hydrogen, fluorine, chlorine, bromine, iodine,    trifluoromethyl or trifluoromethoxy,-   R⁷ represents chlorine or bromine,-   R⁹ represents trifluoromethyl, chlorine, bromine, difluoromethoxy or    trifluoroethoxy,-   and at least one active compound of group 2 selected from the    compounds (2-1) to (2-22).

Very particular preference is given active compound combinationscomprising the following compounds of the formula (I-1):

(I-1)

Example No. R² R³ R⁴ R⁵ R⁷ R⁹ m.p. (° C.) I-1-1 H Me Me Cl Cl CF₃185-186 I-1-2 H Me Me Cl Cl OCH₂CF₃ 207-208 I-1-3 H Me Me Cl Cl Cl225-226 I-1-4 H Me Me Cl Cl Br 162-164 I-1-5 H Me Cl Cl Cl CF₃ 155-157I-1-6 H Me Cl Cl Cl OCH₂CF₃ 192-195 I-1-7 H Me Cl Cl Cl Cl 205-206 I-1-8H Me Cl Cl Cl Br 245-246 I-1-9 H i-Pr Me Cl Cl CF₃ 195-196 I-1-10 H i-PrMe Cl Cl OCH₂CF₃ 217-218 I-1-11 H i-Pr Me Cl Cl Cl 173-175 I-1-12 H i-PrMe Cl Cl Br 159-161 I-1-13 H i-Pr Cl Cl Cl CF₃ 200-201 I-1-14 H i-Pr ClCl Cl OCH₂CF₃ 232-235 I-1-15 H i-Pr Cl Cl Cl Cl 197-199 I-1-16 H i-Pr ClCl Cl Br 188-190 I-1-17 H Et Me Cl Cl CF₃ 163-164 I-1-18 H Et Me Cl ClOCH₂CF₃ 205-207 I-1-19 H Et Me Cl Cl Cl 199-200 I-1-20 H Et Me Cl Cl Br194-195 I-1-21 H Et Cl Cl Cl CF₃ 201-202 I-1-22 H Et Cl Cl Cl Cl 206-208I-1-23 H Et Cl Cl Cl Br 214-215 I-1-24 H t-Bu Me Cl Cl CF₃ 223-225I-1-25 H t-Bu Me Cl Cl Cl 163-165 I-1-26 H t-Bu Me Cl Cl Br 159-161I-1-27 H t-Bu Cl Cl Cl CF₃ 170-172 I-1-28 H t-Bu Cl Cl Cl Cl 172-173I-1-29 H t-Bu Cl Cl Cl Br 179-180 I-1-30 H Me Me Br Cl CF₃ 222-223I-1-31 H Et Me Br Cl CF₃ 192-193 I-1-32 H i-Pr Me Br Cl CF₃ 197-198I-1-33 H t-Bu Me Br Cl CF₃ 247-248 I-1-34 H Me Me Br Cl Cl 140-141I-1-35 H Et Me Br Cl Cl 192-194 I-1-36 H i-Pr Me Br Cl Cl 152-153 I-1-37H t-Bu Me Br Cl Cl 224-225 I-1-38 H Me Me Br Cl Br 147-149 I-1-39 H EtMe Br Cl Br 194-196 I-1-40 H i-Pr Me Br Cl Br 185-187 I-1-41 H t-Bu MeBr Cl Br 215-221 I-1-42 H Me Me I Cl CF₃ 199-200 I-1-43 H Et Me I Cl CF₃199-200 I-1-44 H i-Pr Me I Cl CF₃ 188-189 I-1-45 H t-Bu Me I Cl CF₃242-243 I-1-46 H Me Me I Cl Cl 233-234 I-1-47 H Et Me I Cl Cl 196-197I-1-48 H i-Pr Me I Cl Cl 189-190 I-1-49 H t-Bu Me I Cl Cl 228-229 I-1-50H Me Me I Cl Br 229-230 I-1-51 H iPr Me I Cl Br 191-192 I-1-52 H Me BrBr Cl CF₃ 162-163 I-1-53 H Et Br Br Cl CF₃ 188-189 I-1-54 H i-Pr Br BrCl CF₃ 192-193 I-1-55 H t-Bu Br Br Cl CF₃ 246-247 I-1-56 H Me Br Br ClCl 188-190 I-1-57 H Et Br Br Cl Cl 192-194 I-1-58 H i-Pr Br Br Cl Cl197-199 I-1-59 H t-Bu Br Br Cl Cl 210-212 I-1-60 H Me Br Br Cl Br166-168 I-1-61 H Et Br Br Cl Br 196-197 I-1-62 H i-Pr Br Br Cl Br162-163 I-1-63 H t-Bu Br Br Cl Br 194-196 I-1-64 H t-Bu Cl Br Cl CF₃143-145 I-1-65 Me Me Br Br Cl Cl 153-155 I-1-66 Me Me Me Br Cl CF₃207-208 I-1-67 Me Me Cl Cl Cl Cl 231-232 I-1-68 Me Me Br Br Cl Br189-190 I-1-69 Me Me Cl Cl Cl Br 216-218 I-1-70 Me Me Cl Cl Cl CF₃225-227 I-1-71 Me Me Br Br Cl CF₃ 228-229 I-1-72 H i-Pr Me H Cl CF₃237-239and at least one active compound of group 2 selected from the compounds(2-1) to (2-22).

Especially preferred are active compound combinations comprising acompound of the formulae below

and at least one active compound of group 2 selected from the compounds(2-1) to (2-22).

Preference is given to active compound combinations which preferablycomprise the following active compounds of group 2:

-   (2-5) triflumuron-   (2-9) emamectin-   (2-10) methoxyfenozide-   (2-16) fipronil-   (2-17) ethiprole-   (2-21) indoxacarb-   (2-22) flufenoxuron.

Emphasis is given to the following specifically mentioned activecompound combinations (2-component mixtures) comprising a compound ofthe formula (I-1) and the stated active compound of group 2:

Active compound combination No. comprising  1a) (I-1-1) and (2-5)triflumuron  1b) (I-1-1) and (2-9) emamectin  1c) (I-1-1) and (2-10)methoxyfenozide  1d) (I-1-1) and (2-16) fipronil  1e) (I-1-1) and (2-17)ethiprole  1f) (I-1-1) and (2-21) indoxacarb  1g) (I-1-1) and (2-22)flufenoxuron  2a) (I-1-2) and (2-5) triflumuron  2b) (I-1-2) and (2-9)emamectin  2c) (I-1-2) and (2-10) methoxyfenozide  2d) (I-1-2) and(2-16) fipronil  2e) (I-1-2) and (2-17) ethiprole  2f) (I-1-2) and(2-21) indoxacarb  2g) (I-1-2) and (2-22) flufenoxuron  3a) (I-1-3) and(2-5) triflumuron  3b) (I-1-3) and (2-9) emamectin  3c) (I-1-3) and(2-10) methoxyfenozide  3d) (I-1-3) and (2-16) fipronil  3e) (I-1-3) and(2-17) ethiprole  3f) (I-1-3) and (2-21) indoxacarb  3g) (I-1-3) and(2-22) flufenoxuron  4a) (I-1-4) and (2-5) triflumuron  4b) (I-1-4) and(2-9) emamectin  4c) (I-1-4) and (2-10) methoxyfenozide  4d) (I-1-4) and(2-16) fipronil  4e) (I-1-4) and (2-17) ethiprole  4f) (I-1-4) and(2-21) indoxacarb  4g) (I-1-4) and (2-22) flufenoxuron  5a) (I-1-5) and(2-5) triflumuron  5b) (I-1-5) and (2-9) emamectin  5c) (I-1-5) and(2-10) methoxyfenozide  5d) (I-1-5) and (2-16) fipronil  5e) (I-1-5) and(2-17) ethiprole  5f) (I-1-5) and (2-21) indoxacarb  5g) (I-1-5) and(2-22) flufenoxuron  6a) (I-1-6) and (2-5) triflumuron  6b) (I-1-6) and(2-9) emamectin  6c) (I-1-6) and (2-10) methoxyfenozide  6d) (I-1-6) and(2-16) fipronil  6e) (I-1-6) and (2-17) ethiprole  6f) (I-1-6) and(2-21) indoxacarb  6g) (I-1-6) and (2-22) flufenoxuron  7a) (I-1-7) and(2-5) triflumuron  7b) (I-1-7) and (2-9) emamectin  7c) (I-1-7) and(2-10) methoxyfenozide  7d) (I-1-7) and (2-16) fipronil  7e) (I-1-7) and(2-17) ethiprole  7f) (I-1-7) and (2-21) indoxacarb  7g) (I-1-7) and(2-22) flufenoxuron  8a) (I-1-8) and (2-5) triflumuron  8b) (I-1-8) and(2-9) emamectin  8c) (I-1-8) and (2-10) methoxyfenozide  8d) (I-1-8) and(2-16) fipronil  8e) (I-1-8) and (2-17) ethiprole  8f) (I-1-8) and(2-21) indoxacarb  8g) (I-1-8) and (2-22) flufenoxuron  9a) (I-1-9) and(2-5) triflumuron  9b) (I-1-9) and (2-9) emamectin  9c) (I-1-9) and(2-10) methoxyfenozide  9d) (I-1-9) and (2-16) fipronil  9e) (I-1-9) and(2-17) ethiprole  9f) (I-1-9) and (2-21) indoxacarb  9g) (I-1-9) and(2-22) flufenoxuron 10a) (I-1-11) and (2-5) triflumuron 10b) (I-1-11)and (2-9) emamectin 10c) (I-1-11) and (2-10) methoxyfenozide 10d)(I-1-11) and (2-16) fipronil 10e) (I-1-11) and (2-17) ethiprole 10f)(I-1-11) and (2-21) indoxacarb 10g) (I-1-11) and (2-22) flufenoxuron11a) (I-1-12) and (2-5) triflumuron 11b) (I-1-12) and (2-9) emamectin11c) (I-1-12) and (2-10) methoxyfenozide 11d) (I-1-12) and (2-16)fipronil 11e) (I-1-12) and (2-17) ethiprole 11f) (I-1-12) and (2-21)indoxacarb 11g) (I-1-12) and (2-22) flufenoxuron 12a) (I-1-13) and (2-5)triflumuron 12b) (I-1-13) and (2-9) emamectin 12c) (I-1-13) and (2-10)methoxyfenozide 12d) (I-1-13) and (2-16) fipronil 12e) (I-1-13) and(2-17) ethiprole 12f) (I-1-13) and (2-21) indoxacarb 12g) (I-1-13) and(2-22) flufenoxuron 13a) (I-1-15) and (2-5) triflumuron 13b) (I-1-15)and (2-9) emamectin 13c) (I-1-15) and (2-10) methoxyfenozide 13d)(I-1-15) and (2-16) fipronil 13e) (I-1-15) and (2-17) ethiprole 13f)(I-1-15) and (2-21) indoxacarb 13g) (I-1-15) and (2-22) flufenoxuron14a) (I-1-16) and (2-5) triflumuron 14b) (I-1-16) and (2-9) emamectin14c) (I-1-16) and (2-10) methoxyfenozide 14d) (I-1-16) and (2-16)fipronil 14e) (I-1-16) and (2-17) ethiprole 14f) (I-1-16) and (2-21)indoxacarb 14g) (I-1-16) and (2-22) flufenoxuron 15a) (I-1-19) and (2-5)triflumuron 15b) (I-1-19) and (2-9) emamectin 15c) (I-1-19) and (2-10)methoxyfenozide 15d) (I-1-19) and (2-16) fipronil 15e) (I-1-19) and(2-17) ethiprole 15f) (I-1-19) and (2-21) indoxacarb 15g) (I-1-19) and(2-22) flufenoxuron 16a) (I-1-21) and (2-5) triflumuron 16b) (I-1-21)and (2-9) emamectin 16c) (I-1-21) and (2-10) methoxyfenozide 16d)(I-1-21) and (2-16) fipronil 16e) (I-1-21) and (2-17) ethiprole 16f)(I-1-21) and (2-21) indoxacarb 16g) (I-1-21) and (2-22) flufenoxuron17a) (I-1-22) and (2-5) triflumuron 17b) (I-1-22) and (2-9) emamectin17c) (I-1-22) and (2-10) methoxyfenozide 17d) (I-1-22) and (2-16)fipronil 17e) (I-1-22) and (2-17) ethiprole 17f) (I-1-22) and (2-21)indoxacarb 17g) (I-1-22) and (2-22) flufenoxuron 18a) (I-1-23) and (2-5)triflumuron 18b) (I-1-23) and (2-9) emamectin 18c) (I-1-23) and (2-10)methoxyfenozide 18d) (I-1-23) and (2-16) fipronil 18e) (I-1-23) and(2-17) ethiprole 18f) (I-1-23) and (2-21) indoxacarb 18g) (I-1-23) and(2-22) flufenoxuron 19a) (I-1-24) and (2-5) triflumuron 19b) (I-1-24)and (2-9) emamectin 19c) (I-1-24) and (2-10) methoxyfenozide 19d)(I-1-24) and (2-16) fipronil 19e) (I-1-24) and (2-17) ethiprole 19f)(I-1-24) and (2-21) indoxacarb 19g) (I-1-24) and (2-22) flufenoxuron20a) (I-1-26) and (2-5) triflumuron 20b) (I-1-26) and (2-9) emamectin20c) (I-1-26) and (2-10) methoxyfenozide 20d) (I-1-26) and (2-16)fipronil 20e) (I-1-26) and (2-17) ethiprole 20f) (I-1-26) and (2-21)indoxacarb 20g) (I-1-26) and (2-22) flufenoxuron 21a) (I-1-27) and (2-5)triflumuron 21b) (I-1-27) and (2-9) emamectin 21c) (I-1-27) and (2-10)methoxyfenozide 21d) (I-1-27) and (2-16) fipronil 21e) (I-1-27) and(2-17) ethiprole 21f) (I-1-27) and (2-21) indoxacarb 21g) (I-1-27) and(2-22) flufenoxuron 22a) (I-1-29) and (2-5) triflumuron 22b) (I-1-29)and (2-9) emamectin 22c) (I-1-29) and (2-10) methoxyfenozide 22d)(I-1-29) and (2-16) fipronil 22e) (I-1-29) and (2-17) ethiprole 22f)(I-1-29) and (2-21) indoxacarb 22g) (I-1-29) and (2-22) flufenoxuron23a) (I-1-30) and (2-5) triflumuron 23b) (I-1-30) and (2-9) emamectin23c) (I-1-30) and (2-10) methoxyfenozide 23d) (I-1-30) and (2-16)fipronil 23e) (I-1-30) and (2-17) ethiprole 23f) (I-1-30) and (2-21)indoxacarb 23g) (I-1-30) and (2-22) flufenoxuron 24a) (I-1-31) and (2-5)triflumuron 24b) (I-1-31) and (2-9) emamectin 24c) (I-1-31) and (2-10)methoxyfenozide 24d) (I-1-31) and (2-16) fipronil 24e) (I-1-31) and(2-17) ethiprole 24f) (I-1-31) and (2-21) indoxacarb 24g) (I-1-31) and(2-22) flufenoxuron 25a) (I-1-32) and (2-5) triflumuron 25b) (I-1-32)and (2-9) emamectin 25c) (I-1-32) and (2-10) methoxyfenozide 25d)(I-1-32) and (2-16) fipronil 25e) (I-1-32) and (2-17) ethiprole 25f)(I-1-32) and (2-21) indoxacarb 25g) (I-1-32) and (2-22) flufenoxuron26a) (I-1-33) and (2-5) triflumuron 26b) (I-1-33) and (2-9) emamectin26c) (I-1-33) and (2-10) methoxyfenozide 26d) (I-1-33) and (2-16)fipronil 26e) (I-1-33) and (2-17) ethiprole 26f) (I-1-33) and (2-21)indoxacarb 26g) (I-1-33) and (2-22) flufenoxuron 27a) (I-1-38) and (2-5)triflumuron 27b) (I-1-38) and (2-9) emamectin 27c) (I-1-38) and (2-10)methoxyfenozide 27d) (I-1-38) and (2-16) fipronil 27e) (I-1-38) and(2-17) ethiprole 27f) (I-1-38) and (2-21) indoxacarb 27g) (I-1-38) and(2-22) flufenoxuron 28a) (I-1-39) and (2-5) triflumuron 28b) (I-1-39)and (2-9) emamectin 28c) (I-1-39) and (2-10) methoxyfenozide 28d)(I-1-39) and (2-16) fipronil 28e) (I-1-39) and (2-17) ethiprole 28f)(I-1-39) and (2-21) indoxacarb 28g) (I-1-39) and (2-22) flufenoxuron29a) (I-1-40) and (2-5) triflumuron 29b) (I-1-40) and (2-9) emamectin29c) (I-1-40) and (2-10) methoxyfenozide 29d) (I-1-40) and (2-16)fipronil 29e) (I-1-40) and (2-17) ethiprole 29f) (I-1-40) and (2-21)indoxacarb 29g) (I-1-40) and (2-22) flufenoxuron 30a) (I-1-42) and (2-5)triflumuron 30b) (I-1-42) and (2-9) emamectin 30c) (I-1-42) and (2-10)methoxyfenozide 30d) (I-1-42) and (2-16) fipronil 30e) (I-1-42) and(2-17) ethiprole 30f) (I-1-42) and (2-21) indoxacarb 30g) (I-1-42) and(2-22) flufenoxuron 31a) (I-1-43) and (2-5) triflumuron 31b) (I-1-43)and (2-9) emamectin 31c) (I-1-43) and (2-10) methoxyfenozide 31d)(I-1-43) and (2-16) fipronil 31e) (I-1-43) and (2-17) ethiprole 31f)(I-1-43) and (2-21) indoxacarb 31g) (I-1-43) and (2-22) flufenoxuron32a) (I-1-44) and (2-5) triflumuron 32b) (I-1-44) and (2-9) emamectin32c) (I-1-44) and (2-10) methoxyfenozide 32d) (I-1-44) and (2-16)fipronil 32e) (I-1-44) and (2-17) ethiprole 32f) (I-1-44) and (2-21)indoxacarb 32g) (I-1-44) and (2-22) flufenoxuron 33a) (I-1-50) and (2-5)triflumuron 33b) (I-1-50) and (2-9) emamectin 33c) (I-1-50) and (2-10)methoxyfenozide 33d) (I-1-50) and (2-16) fipronil 33e) (I-1-50) and(2-17) ethiprole 33f) (I-1-50) and (2-21) indoxacarb 33g) (I-1-50) and(2-22) flufenoxuron 34a) (I-1-51) and (2-5) triflumuron 34b) (I-1-51)and (2-9) emamectin 34c) (I-1-51) and (2-10) methoxyfenozide 34d)(I-1-51) and (2-16) fipronil 34e) (I-1-51) and (2-17) ethiprole 34f)(I-1-51) and (2-21) indoxacarb 34g) (I-1-51) and (2-22) flufenoxuron35a) (I-1-52) and (2-5) triflumuron 35b) (I-1-52) and (2-9) emamectin35c) (I-1-52) and (2-10) methoxyfenozide 35d) (I-1-52) and (2-16)fipronil 35e) (I-1-52) and (2-17) ethiprole 35f) (I-1-52) and (2-21)indoxacarb 36g) (I-1-52) and (2-22) flufenoxuron 36a) (I-1-53) and (2-5)triflumuron 36b) (I-1-53) and (2-9) emamectin 36c) (I-1-53) and (2-10)methoxyfenozide 36d) (I-1-53) and (2-16) fipronil 36e) (I-1-53) and(2-17) ethiprole 36f) (I-1-53) and (2-21) indoxacarb 36g) (I-1-53) and(2-22) flufenoxuron 37a) (I-1-54) and (2-5) triflumuron 37b) (I-1-54)and (2-9) emamectin 37c) (I-1-54) and (2-10) methoxyfenozide 37d)(I-1-54) and (2-16) fipronil 37e) (I-1-54) and (2-17) ethiprole 37f)(I-1-54) and (2-21) indoxacarb 37g) (I-1-54) and (2-22) flufenoxuron38a) (I-1-55) and (2-5) triflumuron 38b) (I-1-55) and (2-9) emamectin38c) (I-1-55) and (2-10) methoxyfenozide 38d) (I-1-55) and (2-16)fipronil 38e) (I-1-55) and (2-17) ethiprole 38f) (I-1-55) and (2-21)indoxacarb 38g) (I-1-55) and (2-22) flufenoxuron 39a) (I-1-56) and (2-5)triflumuron 39b) (I-1-56) and (2-9) emamectin 39c) (I-1-56) and (2-10)methoxyfenozide 39d) (I-1-56) and (2-16) fipronil 39e) (I-1-56) and(2-17) ethiprole 39f) (I-1-56) and (2-21) indoxacarb 39g) (I-1-56) and(2-22) flufenoxuron 40a) (I-1-57) and (2-5) triflumuron 40b) (I-1-57)and (2-9) emamectin 40c) (I-1-57) and (2-10) methoxyfenozide 40d)(I-1-57) and (2-16) fipronil 40e) (I-1-57) and (2-17) ethiprole 40f)(I-1-57) and (2-21) indoxacarb 40g) (I-1-57) and (2-22) flufenoxuron41a) (I-1-58) and (2-5) triflumuron 41b) (I-1-58) and (2-9) emamectin41c) (I-1-58) and (2-10) methoxyfenozide 41d) (I-1-58) and (2-16)fipronil 41e) (I-1-58) and (2-17) ethiprole 41f) (I-1-58) and (2-21)indoxacarb 41g) (I-1-58) and (2-22) flufenoxuron 42a) (I-1-60) and (2-5)triflumuron 42b) (I-1-60) and (2-9) emamectin 42c) (I-1-60) and (2-10)methoxyfenozide 42d) (I-1-60) and (2-16) fipronil 42e) (I-1-60) and(2-17) ethiprole 42f) (I-1-60) and (2-21) indoxacarb 42g) (I-1-60) and(2-22) flufenoxuron 43a) (I-1-61) and (2-5) triflumuron 43b) (I-1-61)and (2-9) emamectin 43c) (I-1-61) and (2-10) methoxyfenozide 43d)(I-1-61) and (2-16) fipronil 43e) (I-1-61) and (2-17) ethiprole 43f)(I-1-61) and (2-21) indoxacarb 43g) (I-1-61) and (2-22) flufenoxuron44a) (I-1-62) and (2-5) triflumuron 44b) (I-1-62) and (2-9) emamectin44c) (I-1-62) and (2-10) methoxyfenozide 44d) (I-1-62) and (2-16)fipronil 44e) (I-1-62) and (2-17) ethiprole 44f) (I-1-62) and (2-21)indoxacarb 44g) (I-1-62) and (2-22) flufenoxuron 45a) (I-1-64) and (2-5)triflumuron 45b) (I-1-64) and (2-9) emamectin 45c) (I-1-64) and (2-10)methoxyfenozide 45d) (I-1-64) and (2-16) fipronil 45e) (I-1-64) and(2-17) ethiprole 45f) (I-1-64) and (2-21) indoxacarb 46g) (I-1-64) and(2-22) flufenoxuron 46a) (I-1-65) and (2-5) triflumuron 46b) (I-1-65)and (2-9) emamectin 46c) (I-1-65) and (2-10) methoxyfenozide 46d)(I-1-65) and (2-16) fipronil 46e) (I-1-65) and (2-17) ethiprole 46f)(I-1-65) and (2-21) indoxacarb 46g) (I-1-65) and (2-22) flufenoxuron47a) (I-1-66) and (2-5) triflumuron 47b) (I-1-66) and (2-9) emamectin47c) (I-1-66) and (2-10) methoxyfenozide 47d) (I-1-66) and (2-16)fipronil 47e) (I-1-66) and (2-17) ethiprole 47f) (I-1-66) and (2-21)indoxacarb 47g) (I-1-66) and (2-22) flufenoxuron 48a) (I-1-67) and (2-5)triflumuron 48b) (I-1-67) and (2-9) emamectin 48c) (I-1-67) and (2-10)methoxyfenozide 48d) (I-1-67) and (2-16) fipronil 48e) (I-1-67) and(2-17) ethiprole 48f) (I-1-67) and (2-21) indoxacarb 48g) (I-1-67) and(2-22) flufenoxuron 49a) (I-1-68) and (2-5) triflumuron 49b) (I-1-68)and (2-9) emamectin 49c) (I-1-68) and (2-10) methoxyfenozide 49d)(I-1-68) and (2-16) fipronil 49e) (I-1-68) and (2-17) ethiprole 49f)(I-1-68) and (2-21) indoxacarb 49g) (I-1-68) and (2-22) flufenoxuron50a) (I-1-69) and (2-5) triflumuron 50b) (I-1-69) and (2-9) emamectin50c) (I-1-69) and (2-10) methoxyfenozide 50d) (I-1-69) and (2-16)fipronil 50e) (I-1-69) and (2-17) ethiprole 50f) (I-1-69) and (2-21)indoxacarb 50g) (I-1-69) and (2-22) flufenoxuron 51a) (I-1-70) and (2-5)triflumuron 51b) (I-1-70) and (2-9) emamectin 51c) (I-1-70) and (2-10)methoxyfenozide 51d) (I-1-70) and (2-16) fipronil 51e) (I-1-70) and(2-17) ethiprole 51f) (I-1-70) and (2-21) indoxacarb 51g) (I-1-70) and(2-22) flufenoxuron 52a) (I-1-71) and (2-5) triflumuron 52b) (I-1-71)and (2-9) emamectin 52c) (I-1-71) and (2-10) methoxyfenozide 52d)(I-1-71) and (2-16) fipronil 52e) (I-1-71) and (2-17) ethiprole 52f)(I-1-71) and (2-21) indoxacarb 52g) (I-1-71) and (2-22) flufenoxuron53a) (I-1-72) and (2-5) triflumuron 53b) (I-1-72) and (2-9) emamectin53c) (I-1-72) and (2-10) methoxyfenozide 53d) (I-1-72) and (2-16)fipronil 53e) (I-1-72) and (2-17) ethiprole 53f) (I-1-72) and (2-21)indoxacarb 53g) (I-1-72) and (2-22) flufenoxuron

However, the general or preferred radical definitions or illustrationsgiven above can also be combined with one another as desired, i.e.including combinations between the respective ranges and preferredranges. They apply both to the end products and, correspondingly, toprecursors and intermediates.

Preference according to the invention is given to active compoundcombinations comprising compounds of the formula (I) and activecompounds of the formulae (2-1) to (2-22) in which the individualradicals are a combination of the meanings listed above as beingpreferred (preferable).

Particular preference according to the invention is given to activecompound combinations comprising compounds of the formula (I) and activecompounds of the formulae (2-1) to (2-22) in which the individualradicals are a combination of the meanings listed above as beingparticularly preferred.

Very particular preference according to the invention is given to activecompound combinations comprising compounds of the formula (I) and activecompounds of the formulae (2-1) to (2-22) in which the individualradicals are a combination of the meanings listed above as being veryparticularly preferred.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl,can in each case be straight-chain or branched as far as this ispossible, including in combination with heteroatoms, such as, forexample, in alkoxy.

Optionally substituted radicals can be mono- or polysubstituted, wherein the case of polysubstitutions the substituents can be identical ordifferent.

In addition, the active compound combinations may also comprise furtherfungicidally, acaricidally or insecticidally active cocomponents.

If the active compounds in the active compound combinations according tothe invention are present in certain weight ratios, the synergisticeffect is particularly pronounced. The mixing ratios preferred forfinding the synergism are not necessarily the preferred mixing ratiosrelevant for 100% activity. However, the weight ratios of the activecompounds in the active compound combinations can be varied within arelatively wide range. In general, the combinations according to theinvention comprise active compounds of the formula (I) and the mixingpartner of group 2 in the stated preferred and particularly preferredmixing ratios:

The mixing ratios are based on weight ratios. The ratio is to beunderstood as meaning active compound of the formula (I): mixing partner

Particularly preferred mixing Mixing partner Preferred mixing ratioratio chlorfluazuron 10:1 to 1:10 5:1 to 1:5 diflubenzuron 10:1 to 1:105:1 to 1:5 lufenuron 20:1 to 1:5  10:1 to 1:2  teflubenzuron 20:1 to1:5  10:1 to 1:2  triflumuron 10:1 to 1:10 5:1 to 1:5 novaluron 10:1 to1:10 5:1 to 1:5 hexaflumuron 20:1 to 1:5  5:1 to 1:2 bistrifluoron 10:1to 1:10 5:1 to 1:5 flufenoxuron 50:1 to 1:5  10:1 to 1:1  emamectin 50:1to 1:5  10:1 to 1:1  methoxyfenozide 10:1 to 1:10 5:1 to 1:5tebufenozide 10:1 to 1:10 5:1 to 1:5 halofenozide  2:1 to 1:100  1:1 to1:30 chromafenozide 10:1 to 1:10 5:1 to 1:5 Trichogramma spp. 1000 ga.i./ha:20 000 wasps/ha 300 g a.i./ha:50 000 wasps/ha to to 10 ga.i./ha:500 000 wasps/ha 50 g a.i./ha:300 000 wasps/ha Verticilliumlecanii 0.05% a.i.:0.05% F⁽*⁾ to 0.001% 0.03% a.i.:0.1% F⁽*⁾ to 0.005%a.i.:0.5% F⁽*⁾ a.i.:0.2% F⁽*⁾ fipronil 10:1 to 1:10 5:1 to 1:5 ethiprole10:1 to 1:10 5:1 to 1:5 cyromazine 10:1 to 1:10 5:1 to 1:5 azadirachtin50:1 to 1:5  10:1 to 1:1  diofenolan 100:1 to 1:2  20:1 to 1:1 indoxacarb 50:1 to 1:5  20:1 to 1:2  F⁽*⁾ Formulation comprising 10⁹ to10¹⁰ spores/g

The active compound combinations of the invention are suitable forcontrolling animal pests, preferably arthropods and nematodes, inparticular insects and arachnids, found in agriculture, in animalhealth, in forests, in the protection of stored products and materialsand in the hygiene sector. They are active against normally sensitiveand resistant species, and against all or individual developmentalstages. The abovementioned pests include:

From the order of the Isopoda, for example, Oniscus asellus,Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus.

From the order of the Chilopoda, for example, Geophilus carpophagus,Scutigera spp.

From the order of the Symphyla, for example, Scutigerella immaculata.

From the order of the Thysanura, for example, Lepisma saccharina.

From the order of the Collembola, for example, Onychiurus armatus.

From the order of the Orthoptera, for example, Acheta domesticus,Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus spp.,Schistocerca gregaria.

From the order of the Blattaria, for example, Blatta orientalis,Periplaneta americana, Leucophaea maderae, Blattella germanica.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Reticulitermes spp.

From the order of the Phthiraptera, for example, Pediculus humanuscorporis, Haematopinus spp., Linognathus spp., Trichodectes spp.,Damalinia spp.

From the order of the Thysanoptera, for example, Hercinothripsfemoralis, Thrips tabaci, Thrips palmi, Frankliniella accidentalis.

From the order of the Heteroptera, for example, Eurygaster spp.,Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodniusprolixus, Triatoma spp.

From the order of the Homoptera, for example, Aleurodes brassicae,Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicorynebrassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosomalanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus spp.,Macrosiphum avenae, Myzus spp., Phorodon humuli, Rhopalosiphum padi,Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecaniumcorni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens,Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.

From the order of the Lepidoptera, for example, Pectinophoragossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletisblancardella, Hyponomeuta padella, Plutella xylostella, Malacosomaneustria, Euproctis chrysorrhoea, Lymantria spp., Bucculatrixthurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltiaspp., Earias insulana, Heliothis spp., Mamestra brassicae, Panolisflammea, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pierisspp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleriamellonella, Tineola bisselliella, Tinea pellionella, Hofmannophilapseudospretella, Cacoecia podana, Capua reticulana, Choristoneurafumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana,Cnaphalocerus spp., Oulema oryzae.

From the order of the Coleoptera, for example, Anobium punctatum,Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus,Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedoncochleariae, Diabrotica spp., Psylliodes chrysocephala, Epilachnavarivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp.,Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus,Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogodermaspp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus,Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp.,Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha,Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrusoryzophilus.

From the order of the Hymenoptera, for example, Diprion spp., Hoplocampaspp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera, for example, Aedes spp., Anopheles spp.,Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphoraerythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp.,Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp.,Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinellafrit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae,Tipula paludosa, Hylemyia spp., Liriomyza spp.

From the order of the Siphonaptera, for example, Xenopsylla cheopis,Ceratophyllus spp.

From the class of the Arachnida, for example, Scorpio maurus,Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp.,Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora,Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp.,Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemusspp., Bryobia praetiosa, Panonychus spp., Tetranychus spp.,Hemitarsonemus spp., Brevipalpus spp.

The plant-parasitic nematodes include, for example, Pratylenchus spp.,Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans,Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp.,Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.

The active compound combinations of the invention can be converted intothe customary formulations such as solutions, emulsions, wettablepowders, suspensions, powders, dusts, pastes, soluble powders, granules,suspension-emulsion concentrates, natural and synthetic materialsimpregnated with active compound, and microencapsulations in polymericmaterials.

These formulations are produced in a known manner, for example by mixingthe active compounds with extenders, that is, liquid solvents and/orsolid carriers, optionally with the use of surfactants, that is,emulsifiers and/or dispersants, and/or foam formers.

If the extender used is water, it is also possible, for example, to useorganic solvents as cosolvents. The following are essentially suitableas liquid solvents: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulfoxide, or else water.

Suitable solid carriers are:

for example ammonium salts and ground natural minerals such as kaolins,clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceousearth, and ground synthetic materials such as finely divided silica,alumina and silicates; suitable solid carriers for granules are: forexample crushed and fractionated natural rocks such as calcite, marble,pumice, sepiolite and dolomite, or else synthetic granules of inorganicand organic meals, and granules of organic material such as sawdust,coconut shells, maize cobs and tobacco stalks; suitable emulsifiersand/or foam formers are: for example nonionic and anionic emulsifierssuch as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcoholethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates, or else protein hydrolysates; suitabledispersants are: for example lignin-sulfite waste liquors andmethylcellulose.

Tackifiers such as carboxymethylcellulose and natural and syntheticpolymers in the form of powders, granules or latices, such as gumarabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for exampleiron oxide, titanium oxide and Prussian Blue, and organic colorants suchas alizarin colorants, azo colorants and metal phthalocyanine colorants,and trace nutrients such as salts of iron, manganese, boron, copper,cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95% by weight ofactive compound, preferably between 0.5 and 90%.

The active compound combinations of the invention can be present intheir commercially available formulations and in the use forms, preparedfrom these formulations, as a mixture with other active compounds, suchas insecticides, attractants, sterilants, bactericides, acaricides,nematicides, fungicides, growth-regulating substances or herbicides. Theinsecticides include, for example, phosphates, carbamates, carboxylates,chlorinated hydrocarbons, phenylureas and substances produced bymicroorganisms, inter alia.

Mixtures with other known active compounds such as herbicides or withfertilizers and growth regulators are also possible.

When used as insecticides, the active compound combinations of theinvention can furthermore be present in their commercially availableformulations and in the use forms, prepared from these formulations, asa mixture with synergists. Synergists are compounds which increase theaction of the active compounds, without it being necessary for thesynergist added to be active itself.

The active compound content of the use forms prepared from thecommercially available formulations can vary within wide limits. Theactive compound concentration of the use forms can be from 0.0000001 to95% by weight of active compound, preferably between 0.0001 and 1% byweight.

The compounds are employed in a customary manner appropriate for the useforms.

When used against hygiene pests and stored-product pests, the activecompound combinations are distinguished by an excellent residual actionon wood and clay as well as good stability to alkali on limedsubstrates.

The active compound combinations of the invention are not only activeagainst plant pests, hygiene pests and stored-product pests, but also,in the veterinary medicine sector, against animal parasites(ectoparasites) such as hard ticks, soft ticks, mange mites, harvestmites, flies (stinging and licking), parasitizing fly larvae, lice, headlice, bird lice and fleas. These parasites include:

From the order of the Anoplurida, for example, Haematopinus spp.,Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.

From the order of the Mallophagida and the suborders Amblycerina andIschnocerina, for example, Trimenopon spp., Menopon spp., Trinoton spp.,Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp.,Trichodectes spp., Felicola spp.

From the order Diptera and the suborders Nematocerina and Brachycerina,for example, Aedes spp., Anopheles spp., Culex spp., Simulium spp.,Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp.,Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopotaspp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp.,Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossinaspp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp.,Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp.,Hippobosca spp., Lipoptena spp., Melophagus spp.

From the order of the Siphonapterida, for example, Pulex spp.,Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp. From the orderof the Heteropterida, for example, Cimex spp., Triatoma spp., Rhodniusspp., Panstrongylus spp.

From the order of the Blattarida, for example, Blatta orientalis,Periplaneta americana, Blattella germanica, Supella spp.

From the subclass of the Acaria (Acarida) and the orders of the Meta-and Mesostigmata, for example, Argas spp., Ornithodorus spp., Otobiusspp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp.,Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp.,Raillietia spp., Pneumonyssus spp., Stemostoma spp., Varroa spp.

From the order of the Actinedida (Prostigmata) and Acaridida(Astigmata), for example, Acarapis spp., Cheyletiella spp.,Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp.,Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp.,Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp.,Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

The active compound combinations of the invention are also suitable forcontrolling arthropods which attack agricultural livestock such as, forexample, cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes,rabbits, chickens, turkeys, ducks, geese, honey bees, other domesticanimals such as, for example, dogs, cats, caged birds, aquarium fish andso-called experimental animals such as, for example, hamsters, guineapigs, rats and mice. By controlling these arthropods, cases of death andreductions in productivity (for meat, milk, wool, hides, eggs, honey andthe like) should be diminished, so that more economical and simpleranimal husbandry is possible by the use of the active compoundcombinations of the invention.

The active compound combinations of the invention are used in theveterinary sector in a known manner by enteral administration in theform of, for example, tablets, capsules, potions, drenches, granules,pastes, boluses, the feed-through method, suppositories, by parenteraladministration such as, for example, by injections (intramuscularly,subcutaneously, intravenously, intraperitoneally and the like),implants, by nasal administration, by dermal administration in the formof, for example, immersing or dipping, spraying, pouring-on,spotting-on, washing, dusting, and with the aid ofactive-compound-comprising molded articles such as collars, ear tags,tail tags, limb bands, halters, marking devices and the like.

When used for cattle, poultry, domestic animals and the like, the activecompound combinations can be applied as formulations (for examplepowders, emulsions, flowables) comprising the active compounds in anamount of 1 to 80% by weight, either directly or after 100- to 10000-fold dilution, or they may be used as a chemical dip.

Moreover, it has been found that the active compound combinations of theinvention show a potent insecticidal action against insects whichdestroy industrial materials.

The following insects may be mentioned by way of example and withpreference, but not by way of limitation:

Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobiumpunctatum, Xestobium rufovillosum, Ptilinus pecticomis, Dendrobiumpertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctusafricanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens,Trogoxylon aequale, Minthes rugicollis, Xyleborus spec., Tryptodendronspec., Apate monachus, Bostrychus capucins, Heterobostrychus brunneus,Sinoxylon spec., Dinoderus minutus.

Dermapterans such as Sirex juvencus, Urocerus gigas, Urocerus gigastaignus, Urocerus augur.

Termites such as Kalotermes flavicollis, Cryptotermes brevis,Heterotermes indicola, Reticulitermes flavipes, Reticulitermessantonensis, Reticulitermes lucifugus, Mastotermes darwiniensis,Zootermopsis nevadensis, Coptotermes formosanus.

Bristle-tails such as Lepisma saccharina.

Industrial materials in the present context are understood as meaningnon-living materials such as, preferably, polymers, adhesives, glues,paper and board, leather, wood, timber products and paints.

The material which is to be protected from insect attack ⁻is veryparticularly preferably wood and timber products.

Wood and timber products which can be protected by the composition ofthe invention, or mixtures comprising it, are to be understood asmeaning, for example:

Construction timber, wooden beams, railway sleepers, bridge components,jetties, vehicles made of wood, boxes, pallets, containers, telephonepoles, wood lagging, windows and doors made of wood, plywood, chipboard,joinery, or timber products which quite generally are used in houseconstruction or building joinery.

The active compound combinations can be used as such, in the form ofconcentrates or generally customary formulations such as powders,granules, solutions, suspensions, emulsions or pastes.

The abovementioned formulations can be prepared in a manner known perse, for example by mixing the active compounds with at least one solventor diluent, emulsifier, dispersant and/or binder or fixative, waterrepellant, if desired desiccants and UV stabilizers, and if desiredcolorants and pigments and other processing auxiliaries.

The insecticidal compositions or concentrates used for protecting woodand timber products comprise the active compound of the invention in aconcentration of 0.0001 to 95% by weight, in particular 0.001 to 60% byweight.

The amount of composition or concentrate employed depends on the speciesand the abundance of the insects and on the medium. The optimal quantityto be employed can be determined in each case by test series uponapplication. In general, however, it will suffice to employ 0.0001 to20% by weight, preferably 0.001 to 10% by weight, of the activecompound, based on the material to be protected.

A suitable solvent and/or diluent is an organochemical solvent orsolvent mixture and/or an oily or oil-type organochemical solvent orsolvent mixture of low volatility and/or a polar organochemical solventor solvent mixture and/or water and, if appropriate, an emulsifierand/or wetter.

Organochemical solvents which are preferably employed are oily oroil-type solvents with an evaporation number of above 35 and a flashpoint of above 30° C., preferably above 45° C. Such oily and oil-typesolvents which are insoluble in water and of low volatility and whichare used are suitable mineral oils or their aromatic fractions ormineral oil-containing solvent mixtures, preferably white spirit,petroleum and/or alkylbenzene.

Mineral oils with a boiling range of 170 to 220° C., white spirit with aboiling range of 170 to 220° C., spindle oil with a boiling range of 250to 350° C., petroleum and aromatics with a boiling range of 160 to 280°C., oil of turpentine, and the like are advantageously used.

In a preferred embodiment, liquid aliphatic hydrocarbons with a boilingrange of 180 to 210° C. or high-boiling mixtures of aromatic andaliphatic hydrocarbons with a boiling range of 180 to 220° C. and/orspindle oil and/or monochloronaphthalene, preferablya-monochloronaphthalene, are used.

The organic oily or oil-type solvents of low volatility and with anevaporation number of above 35 and a flash point of above 30° C.,preferably above 45° C., can be replaced in part by organochemicalsolvents of high or medium volatility, with the proviso that the solventmixture also has an evaporation number of above 35 and a flash point ofabove 30° C., preferably above 45° C., and that the mixture is solubleor emulsifiable in this solvent mixture.

In a preferred embodiment, some of the organochemical solvent or solventmixture is replaced by an aliphatic polar organochemical solvent orsolvent mixture. Aliphatic organochemical solvents which containhydroxyl and/or ester and/or ether groups are preferably used, such as,for example, glycol ethers, esters or the like.

Organochemical binders used for the purposes of the present inventionare the synthetic resins and/or binding drying oils which are known perse and which can be diluted in water and/or dissolved or dispersed oremulsified in the organochemical solvents employed, in particularbinders composed of, or comprising, an acrylate resin, a vinyl resin,for example polyvinyl acetate, polyester resin, polycondensation orpolyaddition resin, polyurethane resin, alkyd resin or modified alkydresin, phenol resin, hydrocarbon resin such as indene/coumarone resin,silicone resin, drying vegetable and/or drying oils and/or physicallydrying binders based on a natural and/or synthetic resin.

The synthetic resin employed as binder can be employed in the form of anemulsion, dispersion or solution. Bitumen or bituminous substances mayalso be used as binders, in amounts of up to 10% by weight. In addition,colorants, pigments, water repellants, odor-masking agents, andinhibitors or anticorrosive agents and the like, all of which are knownper se, can be employed.

In accordance with the invention, the composition or the concentratepreferably comprises, as organochemical binders, at least one alkydresin or modified alkyd resin and/or a drying vegetable oil. Alkydresins which are preferably used in accordance with the invention arethose with an oil content of over 45% by weight, preferably 50 to 68% byweight.

Some or all of the abovementioned binder can be replaced by a fixative(mixture) or plasticizer (mixture). These additives are intended toprevent volatilization of the active compounds, and also crystallizationor precipitation. They preferably replace 0.01 to 30% of the binder(based on 100% of binder employed).

The plasticizers are from the chemical classes of the phthalic esters,such as dibutyl phthalate, dioctyl phthalate or benzyl butyl phthalate,phosphoric esters such as tributyl phosphate, adipic esters such asdi-(2-ethylhexyl)-adipate, stearates such as butyl stearate or amylstearate, oleates such as butyl oleate, glycerol ethers orhigher-molecular-weight glycol ethers, glycerol esters andp-toluenesulfonic esters.

Fixatives are based chemically on polyvinyl alkyl ethers such as, forexample, polyvinyl methyl ether, or ketones such as benzophenone andethylenebenzophenone.

Other suitable solvents or diluents are, in particular, water, ifappropriate as a mixture with one or more of the abovementionedorganochemical solvents or diluents, emulsifiers and dispersants.

Particularly effective timber protection is achieved by industrial-scaleimpregnating processes, for example the vacuum, double-vacuum orpressure processes.

The active compound combinations of the invention can at the same timebe employed for protecting objects which come into contact withsaltwater or brackish water, in particular hulls, screens, nets,buildings, moorings and signaling systems, against fouling.

Fouling by sessile Oligochaeta, such as Serpulidae, and by shells andspecies from the Ledamorpha group (goose barnacles), such as variousLepas and Scalpellum species, or by species from the Balanomorpha group(acorn barnacles), such as Balanus or Pollicipes species, increases thefrictional drag of ships and, as a consequence, leads to a markedincrease in operation costs owing to higher energy consumption andadditionally frequent stops in the dry dock.

Apart from fouling by algae, for example Ectocarpus sp. and Ceramiumsp., fouling by sessile Entomostraka groups, which come under thegeneric term Cirripedia (cirriped crustaceans), is of particularimportance.

Surprisingly, it has now been found that the active compoundcombinations of the invention have an outstanding antifouling action.

Using the active compound combinations of the invention allows the useof heavy metals such as, for example, in bis(trialkyltin) sulfides,tri-n-butyltin laurate, tri-n-butyltin chloride, copper(I) oxide,triethyltin chloride, tri-n-butyl(2-phenyl-4-chlorophenoxy)tin,tributyltin oxide, molybdenum disulfide, antimony oxide, polymeric butyltitanate, phenyl-(bispyridine)-bismuth chloride, tri-n-butyltinfluoride, manganese ethylenebisthiocarbamate, zincdimethyldithiocarbamate, zinc ethylenebisthiocarbamate, zinc salts andcopper salts of 2-pyridinethiol 1-oxide, bisdimethyldithiocarbamoylzincethylenebisthiocarbamate, zinc oxide, copper(1)ethylene-bisdithiocarbamate, copper thiocyanate, copper naphthenate andtributyltin halides to be dispensed with, or the concentration of thesecompounds to be substantially reduced.

If appropriate, the ready-to-use antifouling paints can additionallycomprise other active compounds, preferably algicides, fungicides,herbicides, molluscicides, or other antifouling active compounds.

Preferable suitable components in combinations with the antifoulingcompositions according to the invention are:

-   algicides such as    2-tert-butylamino-4-cyclopropylamino-6-methylthio-1,3,5-triazine,    dichlorophen, diuron, endothal, fentin acetate, isoproturon,    methabenzthiazuron, oxyfluorfen, quinoclamine and terbutryn;-   fungicides such as benzo[b]thiophenecarboxylic acid cyclohexylamide    S,S-dioxide, dichlofluanid, fluorfolpet, 3-iodo-2-propynyl    butylcarbamate, tolylfluanid and azoles such as azaconazole,    cyproconazole, epoxyconazole, hexaconazole, metconazole,    propiconazole and tebuconazole;-   molluscicides such as fentin acetate, metaldehyde, methiocarb,    niclosamid, thiodicarb and trimethacarb;-   or conventional antifouling active compounds such as    4,5-dichloro-2-octyl-4-isothiazolin-3-one, diiodomethylparatryl    sulfone, 2-(N,N-dimethylthiocarbamoylthio)-5-nitrothiazyl,    potassium, copper, sodium and zinc salts of 2-pyridinethiol 1-oxide,    pyridine-triphenylborane, tetrabutyldistannoxane,    2,3,5,6-tetrachloro-4-(methylsulfonyl)-pyridine,    2,4,5,6-tetrachloroisophthalonitrile, tetramethylthiuram disulfide    and 2,4,6-trichlorophenylmaleiimide

The antifouling compositions used comprise the active compoundcombinations of the invention in a concentration of 0.001 to 50% byweight, in particular 0.01 to 20% by weight.

Moreover, the antifouling compositions of the invention comprise thecustomary components such as, for example, those described in Ungerer,Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings,Noyes, Park Ridge, 1973.

Besides the algicidal, fungicidal, molluscicidal active compounds andinsecticidal active compounds of the invention, antifouling paintscomprise, in particular, binders.

Examples of recognized binders are polyvinyl chloride in a solventsystem, chlorinated rubber in a solvent system, acrylic resins in asolvent system, in particular in an aqueous system, vinyl chloride/vinylacetate copolymer systems in the form of aqueous dispersions or in theform of organic solvent systems, butadiene/styrene/acrylonitrilerubbers, drying oils such as linseed oil, resin esters or modifiedhardened resins in combination with tar or bitumens, asphalt and epoxycompounds, small amounts of chlorine rubber, chlorinated polypropyleneand vinyl resins.

If appropriate, paints also comprise inorganic pigments, organicpigments or colorants which are preferably insoluble in salt water.Paints may furthermore comprise materials such as colophonium to allowcontrolled release of the active compounds. Furthermore, the paints maycomprise plasticizers, modifiers which affect the rheological propertiesand other conventional constituents. The compounds of the invention orthe abovementioned mixtures may also be incorporated into self-polishingantifouling systems.

The active compound combinations are also suitable for controllinganimal pests, in particular insects, arachnids and mites, which arefound in enclosed spaces such as, for example, dwellings, factory halls,offices, vehicle cabins and the like. They can be employed in domesticinsecticide products for controlling these pests. They are activeagainst sensitive and resistant species and against all developmentalstages. These pests include:

From the order of the Scorpionidea, for example, Buthus occitanus.

From the order of the Acarina, for example, Argas persicus, Argasreflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus,Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi,Neutrombicula autumnalis, Dermatophagoides pteronissimus,Dermatophagoides forinae.

From the order of the Araneae, for example, Aviculariidae, Araneidae.

From the order of the Opiliones, for example, Pseudoscorpiones chelifer,Pseudoscorpiones cheiridium, Opiliones phalangium.

From the order of the Isopoda, for example, Oniscus asellus, Porcellioscaber.

From the order of the Diplopoda, for example, Blaniulus guttulatus,Polydesmus spp.

From the order of the Chilopoda, for example, Geophilus spp.

From the order of the Zygentoma, for example, Ctenolepisma spp., Lepismasaccharina, Lepismodes inquilinus.

From the order of the Blattaria, for example, Blatta orientalies,Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchloraspp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana,Periplaneta brunnea, Periplaneta fuliginosa, Supella longipalpa.

From the order of the Saltatoria, for example, Acheta domesticus.

From the order of the Dermaptera, for example, Forficula auricularia.

From the order of the Isoptera, for example, Kalotermes spp.,Reticulitermes spp.

From the order of the Psocoptera, for example, Lepinatus spp.,Liposcelis spp.

From the order of the Coleptera, for example, Anthrenus spp., Attagenusspp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp.,Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae,Sitophilus zeamais, Stegobium paniceum.

From the order of the Diptera, for example, Aedes aegypti, Aedesalbopictus, Aedes taeniorhynchus, Anopheles spp., Calliphoraerythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culexpipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Muscadomestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp.,Stomoxys calcitrans, Tipula paludosa.

From the order of the Lepidoptera, for example, Achroia grisella,Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tineapellionella, Tineola bisselliella.

From the order of the Siphonaptera, for example, Ctenocephalides canis,Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsyllacheopis.

From the order of the Hymenoptera, for example, Camponotus herculeanus,Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis,Paravespula spp., Tetramorium caespitum.

From the order of the Anoplura, for example, Pediculus humanus capitis,Pediculus humanus corporis, Phthirus pubis.

From the order of the Heteroptera, for example, Cimex hemipterus, Cimexlectularius, Rhodinus prolixus, Triatoma infestans.

They are used as aerosols, pressureless spray products, for example pumpand atomizer sprays, automatic fogging systems, foggers, foams, gels,evaporator products with evaporator tablets made of cellulose orpolymer, liquid evaporators, gel and membrane evaporators,propeller-driven evaporators, energy-free, or passive, evaporationsystems, moth papers, moth bags and moth gels, as granules or dusts, inbaits for spreading or in bait stations.

According to the invention, it is possible to treat all plants and partsof plants. Plants are to be understood here as meaning all plants andplant populations such as desired and undesired wild plants or cropplants (including naturally occurring crop plants). Crop plants can beplants which can be obtained by conventional breeding and optimizationmethods or by biotechnological and genetic engineering methods orcombinations of these methods, including the transgenic plants andincluding the plant cultivars which can or cannot be protected by plantbreeders' certificates. Parts of plants are to be understood as meaningall above-ground and below-ground parts and organs of plants, such asshoot, leaf, flower and root, examples which may be mentioned beingleaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seedsand also roots, tubers and rhizomes. Parts of plants also includeharvested plants and vegetative and generative propagation material, forexample seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the invention of the plants and parts of plants withthe active compounds is carried out directly or by action on theirenvironment, habitat or storage area according to customary treatmentmethods, for example by dipping, spraying, evaporating, atomizing,broadcasting, brushing-on and, in the case of propagation material, inparticular in the case of seeds, furthermore by one- or multi-layercoating.

As already mentioned above, it is possible to treat all plants and theirparts according to the invention. In a preferred embodiment, wild plantspecies and plant cultivars, or those obtained by conventionalbiological breeding methods, such as crossing or protoplast fusion, andparts thereof, are treated. In a further preferred embodiment,transgenic plants and plant cultivars obtained by genetic engineering,if appropriate in combination with conventional methods (GeneticallyModified Organisms), and parts thereof are treated. The terms “parts”,“parts of plants” and “plant parts” have been explained above.

Particularly preferably, plants of the plant cultivars which are in eachcase commercially available or in use are treated according to theinvention.

Depending on the plant species or plant cultivars, their location andgrowth conditions (soils, climate, vegetation period, diet), thetreatment of the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions which can be used accordingto the invention, better plant growth, increased tolerance to high orlow temperatures, increased tolerance to drought or to water or soilsalt content, increased flowering performance, easier harvesting,accelerated maturation, higher harvest yields, better quality and/or ahigher nutritional value of the harvested products, better storagestability and/or processability of the harvested products are possiblewhich exceed the effects which were actually to be expected.

The transgenic plants or plant cultivars (i.e. those obtained by geneticengineering) which are preferred and to be treated according to theinvention include all plants which, in the genetic modification,received genetic material which imparts particularly advantageous usefultraits to these plants. Examples of such traits are better plant growth,increased tolerance to high or low temperatures, increased tolerance todrought or to water or soil salt content, increased floweringperformance, easier harvesting, accelerated maturation, higher harvestyields, better quality and/or a higher nutritional value of theharvested products, better storage stability and/or processability ofthe harvested products. Further and particularly emphasized examples ofsuch traits are a better defense of the plants against animal andmicrobial pests, such as against insects, mites, phytopathogenic fungi,bacteria and/or viruses, and also increased tolerance of the plants tocertain herbicidally active compounds. Examples of transgenic plantswhich may be mentioned are the important crop plants, such as cereals(wheat, rice), maize, soya beans, potatoes, cotton, tobacco, oilseedrape and also fruit plants (with the fruits apples, pears, citrus fruitsand grapes), and particular emphasis is given to maize, soya beans,potatoes, cotton, tobacco and oilseed rape. Traits that are particularlyemphasized are the increased defense of the plants against insects,arachnids, nematodes and worms by toxins formed in the plants, inparticular those formed in the plants by the genetic material fromBacillus thuringiensis (for example by the genes CryIA(a), CryIA(b),CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF andalso combinations thereof) (hereinbelow referred to as “Bt plants”).Traits that are also particularly emphasized are the increased defenseof plants against fungi, bacteria and viruses by systemic acquiredresistance (SAR), systemin, phytoalexins, elicitors and also resistancegenes and correspondingly expressed proteins and toxins. Traits that arefurthermore particularly emphasized are the increased tolerance of theplants to certain herbicidally active compounds, for exampleimidazolinones, sulfonylureas, glyphosate or phosphinotricin (forexample the “PAT” gene). The genes in question which impart the desiredtraits can also be present in combination with one another in thetransgenic plants. Examples of “Bt plants” which may be mentioned aremaize varieties, cotton varieties, soya bean varieties and potatovarieties which are sold under the trade names YIELD GARD® (for examplemaize, cotton, soya beans), KnockOut® (for example maize), StarLink®(for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf®(potato). Examples of herbicide-tolerant plants which may be mentionedare maize varieties, cotton varieties and soya bean varieties which aresold under the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya beans), Liberty Link® (tolerance tophosphinotricin, for example oilseed rape), IMI® (tolerance toimidazolinones) and STS® (tolerance to sulfonylureas, for examplemaize). Herbicide-resistant plants (plants bred in a conventional mannerfor herbicide tolerance) which may be mentioned include the varietiessold under the name Clearfield® (for example maize). Of course, thesestatements also apply to plant cultivars having these orstill-to-be-developed genetic traits, which plant cultivars will bedeveloped and/or marketed in the future.

The plants listed can be treated according to the invention in aparticularly advantageous manner with the active compound mixtures ofthe invention. The preferred ranges stated above for the mixtures alsoapply to the treatment of these plants. Particular emphasis is given tothe treatment of plants with the mixtures specifically mentioned in thepresent text.

The good insecticidal and acaricidal action of the active compoundcombinations of the invention can be seen from the examples whichfollow. While the individual active compounds show weaknesses in theiraction, the combinations show an action which exceeds a simple sum ofactions.

A synergistic effect in insecticides and acaricides is always presentwhen the action of the active compound combinations exceeds the total ofthe actions of the active compounds when applied individually.

The expected action for a given combination of two active compounds canbe calculated as follows according to S. R. Colby, Weeds, 15 (1967),20-22):

If

-   X is the kill rate, expressed as a percentage of the untreated    control, when employing active compound A at an application rate of    m g/ha or in a concentration of m ppm,-   Y is the kill rate, expressed as a percentage of the untreated    control, when employing active compound B at an application rate of    n g/ha or in a concentration of n ppm and-   E is the kill rate, expressed as a percentage of the untreated    control, when employing active compounds A and B at application    rates of m and n g/ha or in a concentration of m and n ppm,    then

$E = {X + Y - \frac{X \cdot Y}{100}}$

If the actual insecticidal kill rate exceeds the calculated value, theaction of the combination is superadditive, i.e. a synergistic effect ispresent. In this case, the actually observed kill rate must exceed thevalue calculated using the above formula for the expected kill rate (E).

After the desired period of time, the kill in % is determined. 100%means that all animals have been killed; 0% means that none of theanimals have been killed.

USE EXAMPLES Example A

Aphis Gossypii Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cotton leaves (Gossypium hirsutum) which are heavily infested by thecotton aphid (Aphis gossypii) are treated by being dipped into thepreparation of active compound of the desired concentration. After thedesired period of time, the kill in % is determined. 100% means that allaphids have been killed; 0% means that none of the aphids have beenkilled. The determined kill ratios are entered into Colby's formula (seepage 39).

In this test, for example, the following active compound combination inaccordance with the present application shows a synergistically enhancedactivity compared to the active compounds applied on their own:

TABLE A Plant-damaging insects Aphis gossypii test Kill rate in % afterConcentration of active 6^(d) Active compounds compound in ppm found*calc.**

4 10

4 0 (I-1-9) + (2-16) fipronil (1:1) 4 + 4 45 10 *found = activity found**calc. = activity calculated using Colby's formula

Example B Heliothis Armigera Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Soybean shoots (Glycine max) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the cotton bollworm (Heliothis armigera)while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed. The determined kill ratios are enteredinto Colby's formula (see page 39).

In this test, the following active compound combination in accordancewith the present application showed a synergistically enhanced activitycompared to the active compounds applied on their own:

TABLE B 1 Plant-damaging insects Heliothis armigera test Kill rate in %after Concentration of active 6^(d) Active compounds compound in ppmfound* calc.**

0.0064 20

0.8    0 (I-1-9) + (2-5) triflumuron (1:125) 0.0064 + 0.8 65 20 *found =activity found **calc = activity calculated using Colby's formula

TABLE B 2 Plant-damaging insects Heliothis armigera test Kill rate in %after Concentration of active 6^(d) Active compounds compound in ppmfound* calc.**

0.032  0 (2-9) emamectin 0.00128 0 (I-1-9) + (2-9) emamectin (25:1)0.032 + 0.00128 45 0 *found = activity found **calc. = activitycalculated using Colby's formula

TABLE B 3 Plant-damaging insects Heliothis armigera test Kill rate in %after Concentration of active 3^(d) Active compounds compound in ppmfound* calc.**

0.032 45

4    0 (I-1-9) + (2-10) methoxyfenozide (1:125) 0.032 + 4 65 45 *found =activity found **calc. = activity calculated using Colby's formula

Example C

Myzus Persicae Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) which are heavily infested by thegreen peach aphid (Myzus persicae) are treated by being dipped into thepreparation of active compound of the desired concentration.

After the desired period of time, the kill in % is determined. 100%means that all aphids have been killed; 0% means that none of the aphidshave been killed. The determined kill ratios are entered into Colby'sformula (see page 39).

In this test, for example, the following active compound combination inaccordance with the present application shows a synergistically enhancedactivity compared to the active compounds applied on their own:

TABLE C Plant-damaging insects Myzus persicae test Kill rate in % afterConcentration of active 1^(d) Active compounds compound in ppm found*calc.**

20  0

20 50 (I-1-9) + (2-17) ethiprole (1:1) 20 + 20 85 50 *found = activityfound **calc. = activity calculated using Colby's formula

Example D

Phaedon Cochleariae Larvae Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with larvae of the mustard beetle (Phaedon cochleariae) whilethe leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all beetle larvae have been killed; 0% means that none of thebeetle larvae have been killed. The determined kill ratios are enteredinto Colby's formula (see page 39).

In this test, for example, the following active compound combination inaccordance with the present application showed a synergisticallyenhanced activity compared to the active compounds applied on their own:

TABLE D Plant-damaging insects Phaedon cochleariae larvae test Kill ratein % after Concentration of active 6^(d) Active compounds compound inppm found* calc.**

0.0064  0

0.032  10 (I-1-9) + (2-21) indoxacarb (1:5) 0.0064 + 0.032 35 10 *found= activity found **calc. = activity calculated using Colby's formula

Example E

Plutella Xylostella Test (Normally Sensitive Strain)

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the diamondback moth (Plutellaxylostella, normally sensitive strain) while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed. The determined kill ratios are enteredinto Colby's formula (see page 39).

In this test, for example, the following active compound combination inaccordance with the present application showed a synergisticallyenhanced activity compared to the active compounds applied on their own:

TABLE E 1 Plant-damaging insects Plutella xylostella test (normallysensitive strain) Kill rate in % after Concentration of active 6^(d)Active compounds compound in ppm found* calc.**

0.00128  0

0.0064  15 (I-1-9) + (2-16) fipronil (1:5) 0.00128 + 0.0064 95 15 *found= activity found **calc. = activity calculated using Colby's formula

TABLE E 2 Plant-damaging insects Plutella xylostella test (normallysensitive strain) Kill rate in % after Concentration of active 4^(d)Active compounds compound in ppm found* calc.**

0.16 0

20 60 (I-1-9) + (2-5) triflumuron (1:125) 0.16 + 20 100 60 *found =activity found **calc. = activity calculated using Colby's formula

Example F

Plutella Xylostella Test (Resistant Strain)

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the diamondback moth (Plutellaxylostella, resistant strain) while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed. The determined kill ratios are enteredinto Colby's formula (see page 39).

In this test, for example, the following active compound combination inaccordance with the present application showed a synergisticallyenhanced activity compared to the active compounds applied on their own:

TABLE F 1 Plant-damaging insects Plutella xylostella test (resistantstrain) Kill rate in % after Concentration of active 6^(d) Activecompounds compound in ppm found* calc.**

0.032  10 (2-9) emamectin 0.00128 40 (1-1-9) + (2-9) emamectin (25:1)0.032 + 0.00128 65 46 *found = activity found **calc. = activitycalculated using Colby's formula

TABLE F 2 Plant-damaging insects Plutella xylostella test (resistantstrain) Kill rate in% after Concentration of active 4^(d) Activecompounds compound in ppm found* calc.**

0.00128 0

0.0064  0 (I-1-9) + (2-16) fipronil (1:5) 0.00128 + 0.0064 35 0 *found =activity found **calc. = activity calculated using Colby's formula

Example G

Spodoptera Exigua Test

Solvent: 7 parts by weight of dimethylformamide Emulsifier: 2 parts byweight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weightof active compound is mixed with the stated amounts of solvent andemulsifier, and the concentrate is diluted with emulsifier-containingwater to the desired concentration.

Cabbage leaves (Brassica oleracea) are treated by being dipped into thepreparation of active compound of the desired concentration and arepopulated with caterpillars of the beet army worm (Spodoptera exigua)while the leaves are still moist.

After the desired period of time, the kill in % is determined. 100%means that all caterpillars have been killed; 0% means that none of thecaterpillars have been killed. The determined kill ratios are enteredinto Colby's formula (see page 39).

In this test, for example, the following active compound combination inaccordance with the present application showed a synergisticallyenhanced activity compared to the active compounds applied on their own:

TABLE G 1 Plant-damaging insects Spodoptera exigua test Kill rate in %after Concentration of active 6^(d) Active compounds compound in ppmfound* calc.**

0.032 10

0.8  10 (I-1-9) + (2-22) flufenoxuron (1:25) 0.032 + 0.8 60 19 *found =activity found **calc. = activity calculated using Colby's formula

TABLE G 2 Plant-damaging insects Spodoptera exigua test Kill rate in %after Concentration of active 6^(d) Active compounds compound in ppmfound* calc.**

0.0064 15

0.16  70 (1-1-9) + (2-21) indoxacarb (1:25) 0.0064 + 0.16 100 74.5*found = activity found **calc = activity calculated using Colby'sformula

1. A composition comprising a synergistically effective active compoundcombination of anthranilamides of the formula (I)

in which A¹ and A² independently of one another represent oxygen orsulfur, X¹ represents N or CR¹⁰, R¹ represents hydrogen or representsC₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl or C₃-C₆-cycloalkyl, each ofwhich is optionally mono- or polysubstituted, where the substituentsindependently of one another may be selected from the group consistingof R⁶, halogen, cyano, nitro, hydroxyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₂-C₄-alkoxycarbonyl,C₁-C₄-alkylamino, C₂-C₈-dialkylamino, C₃-C₆-cycloalkylamino,(C₁-C₄-alkyl)-C₃-C₆-cycloalkylamino and R¹¹, R² represents hydrogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₄-alkoxy, C₁-C₄-alkylamino, C₂-C₈-dialkylamino,C₃-C₆-cycloalkylamino, C₂-C₆-alkoxycarbonyl or C₂-C₆-alkylcarbonyl, R³represents hydrogen, R¹¹ or represents C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl, C₃-C₆-cycloalkyl, each of which is optionally mono- orpolysubstituted, where the substituents independently of one another maybe selected from the group consisting of R⁶, halogen, cyano, nitro,hydroxyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₂-C₆-alkoxycarbonyl,C₂-C₆-alkylcarbonyl, C₃-C₆-trialkylsilyl, R¹¹, phenyl, phenoxy and a 5-or 6-membered heteroaromatic ring, where each phenyl, phenoxy and 5- or6-membered heteroaromatic ring may optionally be substituted and wherethe substituents independently of one another may be selected from oneto three radicals W or one or more radicals R¹², or R² and R³ may beattached to one another and form the ring M, R⁴ represents hydrogen,C₁-C₆-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₆-cycloalkyl,C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, cyano, nitro, hydroxyl, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl,C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylamino, C₂-C₈-dialkylamino,C₃-C₆-cycloalkylamino, C₃-C₆-trialkylsilyl or represents phenyl, benzylor phenoxy, each of which is optionally mono- or polysubstituted, wherethe substituents independently of one another may be selected from thegroup consisting of C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl,C₃-C₆-cycloalkyl, C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₄-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, cyano, nitro, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,C₁-C₄-alkylsulfonyl, C₁-C₄-alkylamino, C₂-C₈-dialkylamino,C₃-C₆-cycloalkylamino, C₃-C₆-(alkyl)cycloalkylamino,C₂-C₄-alkylcarbonyl, C₂-C₆-alkoxycarbonyl, C₂-C₆-alkylaminocarbonyl,C₃-C₈-dialkylaminocarbonyl and C₃-C₆-trialkylsilyl, R⁵ and R⁸ in eachcase independently of one another represent hydrogen, halogen orrepresent in each case optionally substituted C₁-C₄-alkyl,C₁-C₄-haloalkyl, R¹², G, J, —OJ, —OG, —S(O)_(p)-J, —S(O)_(p)G,—S(O)_(p)-phenyl, where the substituents independently of one anothermay be selected from one to three radicals W or from the groupconsisting of R¹², C₁-C₁₀-alkyl, C₂-C₆-alkenyl, C₂-C₆-alkynyl,C₁-C₄-alkoxy and C₁-C₄-alkylthio, where each substituent may besubstituted by one or more substituents independently of one anotherselected from the group consisting of G, J, R⁶, halogen, cyano, nitro,amino, hydroxyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio,C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylamino,C₂-C₈-dialkylamino, C₃-C₆-trialkylsilyl, phenyl and phenoxy, where eachphenyl or phenoxy ring may optionally be substituted and where thesubstituents independently of one another may be selected from one tothree radicals W or one or more radicals R¹², G in each caseindependently of one another represents a 5- or 6-membered non-aromaticcarbocyclic or heterocyclic ring which may optionally contain one or tworing members from the group consisting of C(═O), SO and S(═O)₂ and whichmay optionally be substituted by one to four substituents independentlyof one another selected from the group consisting of C₁-C₂-alkyl,halogen, cyano, nitro and C₁-C₂-alkoxy, or independently of one anotherrepresents C₂-C₆-alkenyl, C₂-C₆-alkynyl, C₃-C₇-cycloalkyl,(cyano)-C₃-C₇-cycloalkyl, (C₁-C₄-alkyl)-C₃-C₆-cycloalkyl,(C₃-C₆-cycloalkyl)-C₁-C₄-alkyl, where each cycloalkyl, (alkyl)cycloalkyland (cycloalkyl)alkyl may optionally be substituted by one or morehalogen atoms, J in each case independently of one another represents anoptionally substituted 5- or 6-membered heteroaromatic ring, where thesubstituents independently of one another may be selected from one tothree radicals W or one or more radicals R¹², R⁶ independently of oneanother represents —C(=E¹)R¹⁹, -L(=E¹)R¹⁹, —C(=E¹)LR¹⁹, -LC(=E¹)LR¹⁹,—OP(=Q)(OR¹⁹)₂, —SO₂LR¹⁸ or -LSO₂LR¹⁹, where each E¹ independently ofone another represents O, S, N—R¹⁵, N—OR¹⁵, N—N(R¹⁵)₂, N—S═O, N—CN orN—NO₂, R⁷ represents hydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen,C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl,C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl,C₁-C₄-haloalkylsulfonyl, R⁹ represents C₁ -C₄-haloalkyl,C₁-C₄-haloalkoxy, C₁-C₄-haloalkylsulfinyl or halogen, R¹⁰ representshydrogen, C₁-C₄-alkyl, C₁-C₄-haloalkyl, halogen, cyano orC₁-C₄-haloalkoxy, R¹¹ in each case independently of one anotherrepresents in each case optionally mono- to trisubstitutedC₁-C₆-alkylthio, C₁-C₆-alkylsulfenyl, C₁-C₆-haloalkylthio,C₁-C₆-haloalkylsulfenyl, phenylthio or phenylsulfenyl, where thesubstituents independently of one another may be selected from the listW, —S(O)_(n)N(R¹⁶)₂, —C(═O)R¹³, -L(C═O)R¹⁴, —S(C═O)LR¹⁴, —C(═O)LR¹³,—S(O)_(n)NR¹³C(═O)R¹³, —S(O)_(n)NR¹³C(═O)LR¹⁴ or —S(O)_(n)NR¹³S(O)₂LR¹⁴,L in each case independently of one another represents O, NR¹⁸ or S, R¹²in each case independently of one another represents —B(OR¹⁷)₂, amino,SH, thiocyanato, C₃-C₈-trialkylsilyloxy, C₁-C₄-alkyl disulfides, —SF₅,—C(=E¹)R¹⁹, -LC(=E¹)R¹⁹, —C(=E¹)LR¹⁹, -LC(=E¹)LR¹⁹, —OP(=Q)(OR¹⁹)₂,—SO₂LR¹⁹ or -LSO₂LR¹⁹, Q represents O or S, R¹³ in each caseindependently of one another represents hydrogen or represents in eachcase optionally mono- or polysubstituted C₁-C₆-alkyl, C₂-C₆-alkenyl,C₂-C₆-alkynyl or C₃-C₆-cycloalkyl, where the substituents independentlyof one another may be selected from the group consisting of R⁶, halogen,cyano, nitro, hydroxyl, C₁-C₄-alkoxy, C₁-C₄-alkylsulfinyl,C₁-C₄-alkylsulfonyl, C₁-C₄-alkylamino, C₂-C₈-dialkylamino,C₃-C₆-cycloalkylamino or (C₁-C₄-alkyl)-C₃-C₆-cycloalkylamino, R¹⁴ ineach case independently of one another represents in each caseoptionally mono- or polysubstituted C₂-C₂₀-alkenyl, C₂-C₂₀-alkynyl orC₃-C₆-cycloalkyl, where the substituents independently of one anothermay be selected from the group consisting of R⁶, halogen, cyano, nitro,hydroxyl, C₁-C₄-alkoxy, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,C₁-C₄-alkylamino, C₂-C₈-dialkylamino, C₃-C₆-cycloalkylamino and(C₁-C₄-alkyl)-C₃-C₆-cycloalkylamino or represent optionally substitutedphenyl, where the substituents independently of one another may beselected from one to three radicals W or one or more radicals R¹², R¹⁵in each case independently of one another represents hydrogen orrepresents in each case optionally mono- or polysubstitutedC₁-C₆-haloalkyl or C₁-C₆-alkyl, where the substituents independently ofone another may be selected from the group consisting of cyano, nitro,hydroxyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio,C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl, C₁-C₄-alkylamino,C₂-C₈-dialkylamino, C₂-C₆-alkoxycarbonyl, C₂-C₆-alkylcarbonyl,C₃-C₆-trialkylsilyl and optionally substituted phenyl, where thesubstituents independently of one another may be selected from one tothree radicals W or one or more radicals R¹², or N(R¹⁵)₂ represents acycle which forms the ring M, R¹⁶ represents C₁-C₁₂-alkyl orC₁-C₁₂-haloalkyl, or N(R¹⁶)₂ represents a cycle which forms the ring M,R¹⁷ in each case independently of one another represents hydrogen orC₁-C₄-alkyl, or B(OR¹⁷)₂ represents a ring in which the two oxygen atomsare attached via a chain having two to three carbon atoms which areoptionally substituted by one or two substituents independently of oneanother selected from the group consisting of methyl andC₂-C₆-alkoxycarbonyl, R¹⁸ in each case independently of one anotherrepresents hydrogen, C₁-C₆-alkyl or C₁-C₆-haloalkyl, or N(R¹³)(R¹⁸)represents a cycle which forms the ring M, R¹⁹ in each caseindependently of one another represents hydrogen or represents in eachcase mono- or polysubstituted C₁-C₆-alkyl, where the substituentsindependently of one another may be selected from the group consistingof cyano, nitro, hydroxyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy,C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl,C₁-C₄-haloalkylthio, C₁-C₄-haloalkylsulfinyl, C₁-C₄-haloalkylsulfonyl,C₁-C₄-alkylamino, C₂-C₈-dialkylamino, CO₂H, C₂-C₆-alkoxycarbonyl,C₂-C₆-alkylcarbonyl, C₃-C₆-trialkylsilyl and optionally substitutedphenyl, where the substituents independently of one another may beselected from one to three radicals W, C₁-C₆-haloalkyl, C₃-C₆-cycloalkylor phenyl or pyridyl, each of which is optionally mono- totrisubstituted by W, M in each case represents an optionally mono- totetrasubstituted ring which, in addition to the nitrogen atom attachedto the substituent pair R¹³ and R¹⁸, (R¹⁵)₂ or (R¹⁶)₂, contains two tosix carbon atoms and optionally additionally a further nitrogen, sulfuror oxygen atom, where the substituents independently of one another maybe selected from the group consisting of C₁-C₂-alkyl, halogen, cyano,nitro and C₁-C₂-alkoxy, W in each case independently of one anotherrepresents C₁-C₄-alkyl, C₂-C₄-alkenyl, C₂-C₄-alkynyl, C₃-C₆-cycloalkyl,C₁-C₄-haloalkyl, C₂-C₄-haloalkenyl, C₂-C₄-haloalkynyl,C₃-C₆-halocycloalkyl, halogen, cyano, nitro, C₁-C₄-alkoxy,C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfonyl,C₁-C₄-alkylamino, C₂-C₈-dialkylamino, C₃-C₆-cycloalkylamino,(C₁-C₄-alkyl)-C₃-C₆-cycloalkylamino, C₂-C₄-alkylcarbonyl,C₂-C₆-alkoxycarbonyl, CO₂H, C₂-C₆-alkylaminocarbonyl,C₃-C₈-dialkylaminocarbonyl or C₃-C₆-trialkylsilyl, n in each caseindependently of one another represents 0 or 1, p in each caseindependently of one another represents 0, 1 or 2, where, if (a) R⁵represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl, C₂-C₆-haloalkenyl,C₂-C₆-haloalkynyl, C₁-C₄-haloalkoxy, C₁-C₄-haloalkylthio or halogen and(b) R⁸ represents hydrogen, C₁-C₆-alkyl, C₁-C₆-haloalkyl,C₂-C₆-haloalkenyl, C₂-C₆-haloalkynyl, C₁-C₄-haloalkoxy,C₁-C₄-haloalkylthio, halogen, C₂-C₄-alkylcarbonyl, C₂-C₆-alkoxycarbonyl,C₂-C₆-alkylaminocarbonyl or C₃-C₈ dialkylaminocarbonyl, (c) at least onesubstituent selected from the group consisting of R⁶, R¹¹ and R¹² ifpresent and (d) if R¹² is not present, at least one of the radicals R⁶and R¹¹ is different from C₂-C₆-alkylcarbonyl, C₂-C₆-alkoxycarbonyl,C₂-C₆-alkylaminocarbonyl and C₃-C₈-dialkylaminocarbonyl, and where thecompound of the general formula (I) may also be an N-oxide or salt, andat least one insecticidally active compound from groups 2 below,selected from A) benzoylureas, preferably (2-1) chlorfluazuron (knownfrom DE-A 28 18 830)

and/or (2-2) diflubenzuron (known from DE-A 21 23 236)

and/or (2-3) lufenuron (known from EP-A 0 179 022)

and/or (2-4) teflubenzuron (known from EP-A 0 052 833)

and/or (2-5) triflumuron (known from DE-A 26 01 780)

and/or (2-6) novaluron (known from U.S. Pat. No. 4,980,376)

and/or (2-7) hexaflumuron (known from EP-A 0 071 279)

and/or (2-8) bistrifluoron (DBI-3204) (known from WO 98/00394)

and/or (2-22) flufenoxuron (known from EP-A 0 161 019)

and/or B) macrolides, preferably (2-9) emamectin (known from EP-A 0 089202) and/or C) diacylhydrazines, preferably (2-10) methoxyfenozide(known from EP-A 0 639 559)

and/or (2-11) tebufenozide (known from EP-A-339 854)

and/or (2-12) halofenozide (known from EP-A 0 228 564)

and/or (2-13) chromafenozide (ANS-118) (known from EP-A 0 496 342)

and/or (2-14) Trichogramma spp. (known from The Pesticide Manual, 11thEdition, 1997, p. 1236) and/or (2-15) Verticillium lecanii (known fromThe Pesticide Manual, 11th Edition, 1997, p. 1266) and/or (2-16)fipronil (known from EP-A 0 295 117)

and/or (2-17) ethiprole (known from DE-A 196 53 417)

and/or (2-18) cyromazine (known from DE-A 27 36 876)

and/or (2-19) azadirachtin (known from The Pesticide Manual, 11thEdition, 1997, p. 59) and/or (2-20) diofenolan known from DE-A 26 55910)

and/or (2-21) indoxacarb (known from WO 92/11249)


2. The composition as claimed in claim 1 comprising at least one activecompound from the group of the anthranilamides of the formula (I-1) inwhich

in which R² represents hydrogen or C₁-C₆-alkyl, R³ representsC₁-C₆-alkyl which is optionally substituted by one R⁶, R⁴ representsC₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₂-haloalkoxy or halogen, R⁵ representshydrogen, C₁-C₄-alkyl, C₁-C₂-haloalkyl, C₁-C₂-haloalkoxy or halogen, R⁶represents —C(=E²)R¹⁹, -LC(=B²)R¹⁹, —C(=E²)LR¹⁹ or —LC(=E²)LR¹⁹, whereeach E² independently of one another represents O, S, N—R¹⁵, N—OR¹⁵,N—N(R¹⁵)₂, and each L independently of one another represents O or NR¹⁸,R⁷ represents C₁-C₄-haloalkyl or halogen, R⁹ represents C₁-C₂-haloalkyl,C₁-C₂-haloalkoxy, S(O)_(p)—C₁-C₂-haloalkyl or halogen, R¹⁵ in each caseindependently of one another represents hydrogen or represents in eachcase optionally substituted C₁-C₆-haloalkyl or C₁-C₆-alkyl, where thesubstituents independently of one another may be selected from the groupconsisting of cyano, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio,C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-haloalkylthio,C₁-C₄-haloalkylsulfinyl and C₁-C₄-haloalkylsulfonyl, R¹⁸ in each caserepresents hydrogen or C₁-C₄-alkyl, R¹⁹ in each case independently ofone another represents hydrogen or C₁-C₆-alkyl, p independently of oneanother represents 0, 1,
 2. 3. The composition as claimed in claim 1comprising at least one active compound of group 2 selected from (2-5)triflumuron (2-22) flufenoxuron (2-9) emamectin (2-10) methoxyfenozide(2-16) fipronil (2-17) ethiprole (2-21) indoxacarb.
 4. The compositionas claimed in claim 1 comprising anthranilamides of the formula (I) andat least one active compound from group 2 in a ratio of 200:1 to 1:200.5. (canceled)
 6. A process for preparing pesticides, characterized inthat a synergistically effective mixture as defined in claim 1 is mixedwith extenders and/or surfactants.
 7. A method for controlling animalpests, characterized in that synergistically effective mixtures asdefined in claim 1 are allowed to act on animal pests and/or theirhabitat.
 8. The composition as claimed in claim 2 comprisinganthranilamides of the formula (I) and at least one active compound fromgroup 2 in a ratio of 200:1 to 1:200.
 9. The composition as claimed inclaim 3 comprising anthranilamides of the formula (I) and at least oneactive compound from group 2 in a ratio of 200:1 to 1:200.
 10. A processfor preparing pesticides, characterized in that a synergisticallyeffective mixture as defined in claim 2 is mixed with extenders and/orsurfactants.
 11. A process for preparing pesticides, characterized inthat a synergistically effective mixture as defined in claim 3 is mixedwith extenders and/or surfactants.
 12. A process for preparingpesticides, characterized in that a synergistically effective mixture asdefined in claim 4 is mixed with extenders and/or surfactants.
 13. Aprocess for preparing pesticides, characterized in that asynergistically effective mixture as defined in claim 8 is mixed withextenders and/or surfactants.
 14. A process for preparing pesticides,characterized in that a synergistically effective mixture as defined inclaim 9 is mixed with extenders and/or surfactants.
 16. A method forcontrolling animal pests, characterized in that synergisticallyeffective mixtures as defined in claim 2 are allowed to act on animalpests and/or their habitat.
 17. A method for controlling animal pests,characterized in that synergistically effective mixtures as defined inclaim 3 are allowed to act on animal pests and/or their habitat.
 18. Amethod for controlling animal pests, characterized in thatsynergistically effective mixtures as defined in claim 4 are allowed toact on animal pests and/or their habitat.
 19. A method for controllinganimal pests, characterized in that synergistically effective mixturesas defined in claim 8 are allowed to act on animal pests and/or theirhabitat.
 20. A method for controlling animal pests, characterized inthat synergistically effective mixtures as defined in claim 9 areallowed to act on animal pests and/or their habitat.